5-(3-Hydroxypropyl)-2-oxo-4-phenyl-2,5-dihydrofuran-3-yl acetate

Base Information

• Chemical Name: 5-(3-Hydroxypropyl)-2-oxo-4-phenyl-2,5-dihydrofuran-3-yl acetate
• CAS No.: 105364-59-8
• Molecular Formula: C₁₅H₁₆O₅
• Molecular Weight: 276.289
• DSSTox Substance ID: DTXSID30551934
• Mol file: 105364-59-8.mol

Synonyms:105364-59-8;SCHEMBL10776723;DTXSID30551934;XGFXOVTYBNMDBB-UHFFFAOYSA-N;5-(3-Hydroxypropyl)-2-oxo-4-phenyl-2,5-dihydrofuran-3-yl acetate;3-acetoxy-5-(3-hydroxypropyl)-4-phenyl-2(5H)-furanone

Chemical Property of 5-(3-Hydroxypropyl)-2-oxo-4-phenyl-2,5-dihydrofuran-3-yl acetate

Chemical Property:

• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 276.09977361
• Heavy Atom Count: 20
• Complexity: 407

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1=C(C(OC1=O)CCCO)C2=CC=CC=C2

Technology Process of 5-(3-Hydroxypropyl)-2-oxo-4-phenyl-2,5-dihydrofuran-3-yl acetate

There total 13 articles about 5-(3-Hydroxypropyl)-2-oxo-4-phenyl-2,5-dihydrofuran-3-yl acetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

benzyl bromide (100-39-0) → Acetic acid 5-(3-hydroxy-propyl)-2-oxo-4-phenyl-2,5-dihydro-furan-3-yl ester (105364-59-8)

Guidance literature:

Multi-step reaction with 13 steps

1: 97 percent / NaH / tetrahydrofuran / Ambient temperature

2: 99 percent / MCPBA / CH₂Cl₂ / Ambient temperature

3: EtONa / ethanol / Heating

4: 80 percent / aq. NaOH / Heating

5: 77 percent / Me₂NH, AcONa / acetic acid / 100 °C

6: 42 percent / OsO₄,NaIO₄ / dioxane / Ambient temperature

7: 96 percent / H₂ / Pd-black / ethanol

8: 92 percent / Et₃N / tetrahydrofuran / 0 °C

9: 96 percent / CrO₃, H₂SO₄ / acetone; H₂O / 0 °C

10: 71 percent / K₂CO₃ / methanol; H₂O / Ambient temperature

11: pyridine

12: Et₃N / tetrahydrofuran

13: NaBH₄ / tetrahydrofuran

With pyridine; chromium(VI) oxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; sulfuric acid; hydrogen; sodium ethanolate; sodium acetate; sodium hydride; potassium carbonate; dimethyl amine; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium; In tetrahydrofuran; 1,4-dioxane; methanol; sodium hydroxide; ethanol; dichloromethane; water; acetic acid; acetone;

DOI:10.1016/S0040-4039(00)84436-6

Reference yield:

(E)-(5-(benzyloxy)pent-1-en-1-yl)benzene (105364-63-4) → Acetic acid 5-(3-hydroxy-propyl)-2-oxo-4-phenyl-2,5-dihydro-furan-3-yl ester (105364-59-8)

Guidance literature:

Multi-step reaction with 12 steps

1: 99 percent / MCPBA / CH₂Cl₂ / Ambient temperature

2: EtONa / ethanol / Heating

3: 80 percent / aq. NaOH / Heating

4: 77 percent / Me₂NH, AcONa / acetic acid / 100 °C

5: 42 percent / OsO₄,NaIO₄ / dioxane / Ambient temperature

6: 96 percent / H₂ / Pd-black / ethanol

7: 92 percent / Et₃N / tetrahydrofuran / 0 °C

8: 96 percent / CrO₃, H₂SO₄ / acetone; H₂O / 0 °C

9: 71 percent / K₂CO₃ / methanol; H₂O / Ambient temperature

10: pyridine

11: Et₃N / tetrahydrofuran

12: NaBH₄ / tetrahydrofuran

With pyridine; chromium(VI) oxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; sulfuric acid; hydrogen; sodium ethanolate; sodium acetate; potassium carbonate; dimethyl amine; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium; In tetrahydrofuran; 1,4-dioxane; methanol; sodium hydroxide; ethanol; dichloromethane; water; acetic acid; acetone;

DOI:10.1016/S0040-4039(00)84436-6

Reference yield:

(2R,3R)-2-(3-Benzyloxy-propyl)-3-phenyl-oxirane (90055-19-9,105364-64-5) → Acetic acid 5-(3-hydroxy-propyl)-2-oxo-4-phenyl-2,5-dihydro-furan-3-yl ester (105364-59-8)

Guidance literature:

Multi-step reaction with 11 steps

1: EtONa / ethanol / Heating

2: 80 percent / aq. NaOH / Heating

3: 77 percent / Me₂NH, AcONa / acetic acid / 100 °C

4: 42 percent / OsO₄,NaIO₄ / dioxane / Ambient temperature

5: 96 percent / H₂ / Pd-black / ethanol

6: 92 percent / Et₃N / tetrahydrofuran / 0 °C

7: 96 percent / CrO₃, H₂SO₄ / acetone; H₂O / 0 °C

8: 71 percent / K₂CO₃ / methanol; H₂O / Ambient temperature

9: pyridine

10: Et₃N / tetrahydrofuran

11: NaBH₄ / tetrahydrofuran

With pyridine; chromium(VI) oxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; sulfuric acid; hydrogen; sodium ethanolate; sodium acetate; potassium carbonate; dimethyl amine; triethylamine; palladium; In tetrahydrofuran; 1,4-dioxane; methanol; sodium hydroxide; ethanol; water; acetic acid; acetone;

DOI:10.1016/S0040-4039(00)84436-6

upstream raw materials:

benzyl bromide

(E)-(5-(benzyloxy)pent-1-en-1-yl)benzene

3-hydroxy-5-(3-hydroxypropyl)-4-phenyl-2(5H)-furanone

(2R,3R)-2-(3-Benzyloxy-propyl)-3-phenyl-oxirane

Downstream raw materials:

3-acetoxy-5-(3-acetoxypropyl)-4-phenyl-2(5H)-furanone

Refernces