3,4-Dihydro-2h-pyran-2-ylmethyl acetate

Base Information

• Chemical Name: 3,4-Dihydro-2h-pyran-2-ylmethyl acetate
• CAS No.: 22347-71-3
• Molecular Formula: C8H12 O3
• Molecular Weight: 156.181
• NSC Number: 20752
• DSSTox Substance ID: DTXSID70281208
• Nikkaji Number: J749.903E
• Mol file: 22347-71-3.mol

Synonyms:3,4-dihydro-2h-pyran-2-ylmethyl acetate;22347-71-3;2H-Pyran-2-methanol,3,4-dihydro-, 2-acetate;NSC20752;2-acetoxymethyl-3,4-dihydro-2h-pyran;SCHEMBL259449;UVVZLQHUDLXMGT-UHFFFAOYSA-;DTXSID70281208;UVVZLQHUDLXMGT-UHFFFAOYSA-N;NSC-20752;A934017;(+/-)-3,4-dihydro-2H-pyran-2-yl-methyl acetate;InChI=1/C8H12O3/c1-7(9)11-6-8-4-2-3-5-10-8/h3,5,8H,2,4,6H2,1H3

Chemical Property of 3,4-Dihydro-2h-pyran-2-ylmethyl acetate

Chemical Property:

• Vapor Pressure: 0.168mmHg at 25°C
• Boiling Point: 213°Cat760mmHg
• Flash Point: 80.8°C
• Density: 1.052g/cm³
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 156.078644241
• Heavy Atom Count: 11
• Complexity: 163

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1CCC=CO1

Technology Process of 3,4-Dihydro-2h-pyran-2-ylmethyl acetate

There total 6 articles about 3,4-Dihydro-2h-pyran-2-ylmethyl 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: 100.0%

2-hydroxymethyl-3,4-dihydro-2H-pyran (3749-36-8) + acetic anhydride (108-24-7) → acetic acid 3,4-dihydro-2H-pyran-2-ylmethyl ester (22347-71-3)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 17h; Inert atmosphere;

DOI:10.1002/anie.201506944

Reference yield: 90.0%

2-hydroxymethyl-3,4-dihydro-2H-pyran (3749-36-8) + acetyl chloride (75-36-5) → acetic acid 3,4-dihydro-2H-pyran-2-ylmethyl ester (22347-71-3)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 10h; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.orglett.0c02513

Reference yield: 76.0%

trans-6-(phenylsulphonyl)-tetrahydro-2H-pyran-2-methanol acetate (124654-48-4,125375-42-0) → acetic acid 3,4-dihydro-2H-pyran-2-ylmethyl ester (22347-71-3)

Guidance literature:

With triethylamine; magnesium bromide; In tetrahydrofuran; for 18h; ultrasound bath,;

DOI:10.1016/S0040-4020(01)81323-5

upstream raw materials:

2-hydroxymethyl-3,4-dihydro-2H-pyran

acetic anhydride

trans-6-(phenylsulphonyl)-tetrahydro-2H-pyran-2-methanol acetate

acrolein dimer

Downstream raw materials:

trans-6-(benzenesulphonyl)tetrahydro-2H-pyran-2-methanol

cis-methyl 6-<(tert-butyldiphenylsilyloxy)methyl>tetrahydro-α,α-dimethyl-2H-pyran-2-acetate

trans-methyl 6-<(tert-butyldiphenylsilyloxy)methyl>tetrahydro-α,α-dimethyl-2H-pyran-2-acetate

trans-2-(benzenesulphonyl)-6-<(tert-butyldiphenylsilyloxy)methyl>tetrahydro-2H-pyran

Refernces

• 1、 Jagtap, Prakash G.,Chen, Zhiyu,Koppetsch, Karsten,Piro, Elizabeth,Fronce, Paula,Southan, Garry J.,Klotz, Karl-Norbert. "Synthesis of (R)-3,4-dihydro-2H-pyran-2-carboxaldehyde: application to the synthesis of potent adenosine A2A and A3 receptor agonist". . p. 2693 - 2696. Retrieved 2009.
• 2、 Aggarwal, Varinder K.,Madhavachary, Rudrakshula,Noble, Adam,Shu, Chao. "Photoinduced Fragmentation Borylation of Cyclic Alcohols and Hemiacetals". supporting information. p. 7213 - 7218. Retrieved 2020/10/12.
• 3、 -. "AMINOGLYCOSIDES AND USES THEREOF". Paragraph 00972. . Retrieved 2019/03/17.