5-methoxy-3-(3-methylbut-2-enyl)-2-oxindole

Base Information

• Chemical Name: 5-methoxy-3-(3-methylbut-2-enyl)-2-oxindole
• CAS No.: 222533-48-4
• Molecular Formula: C₁₄H₁₇NO₂
• Molecular Weight: 231.294
• Mol file: 222533-48-4.mol

Synonyms:5-methoxy-3-(3-methylbut-2-enyl)-2-oxindole

Chemical Property of 5-methoxy-3-(3-methylbut-2-enyl)-2-oxindole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-methoxy-3-(3-methylbut-2-enyl)-2-oxindole

There total 1 articles about 5-methoxy-3-(3-methylbut-2-enyl)-2-oxindole 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:

5-methoxyindolin-2-one (7699-18-5) + prenyl bromide (870-63-3) → 5-methoxy-3-(3-methylbut-2-enyl)-2-oxindole (222533-48-4)

Guidance literature:

With n-butyllithium; Yield given; Multistep reaction; 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, -78 -> -30 deg C, 2 h;

DOI:10.1021/jo981577q

Reference yield:

5-methoxy-3-(3-methylbut-2-enyl)-2-oxindole (222533-48-4) → 1-benzyl-5-methoxy-1H-spiro[indole-3,3'-pyrrolidin]-2-one

Guidance literature:

Multi-step reaction with 12 steps

1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / Ambient temperature

2: 1.) n-BuLi / 1.) toluene, ether, hexane, -78 -> 0 deg C, 2.) toluene, ether, hexane, -78 -> -10 deg C

3: 95 percent / HCl / methanol

4: 97 percent / NaBH₄ / dioxane; methanol / 1 h

5: 1.) NaH / 1.) DMF, mineral oil, room temperature, 30 min, 2.) DMF, mineral oil, 0 deg C, 5 h

6: 80 percent / sodium nitrite, acetic acid / dimethylsulfoxide / 8 h / 37 °C

7: 1.) triethylamine, diphenylphosphoryl azide / 1.) toluene, reflux, 2 h, 2.) toluene, reflux, 12 h

8: 1.) ozone, 2.) dimethyl sulfide / 1.) ethanol, -78 deg C, 2.) ethanol, room temperature, overnight

9: NaBH₄ / methanol / 1 h

10: triethylamine / CH₂Cl₂ / 1 h / 0 °C

11: NaH / tetrahydrofuran; paraffin / 10 h / Ambient temperature

12: hydrogen / Pd/C / methanol / 8 h / Ambient temperature

With 2,6-dimethylpyridine; hydrogenchloride; sodium tetrahydroborate; n-butyllithium; dimethylsulfide; diphenylphosphoranyl azide; hydrogen; sodium hydride; ozone; acetic acid; triethylamine; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; dimethyl sulfoxide; paraffin;

DOI:10.1021/jo981577q

Reference yield:

5-methoxy-3-(3-methylbut-2-enyl)-2-oxindole (222533-48-4) → (R)-1-benzyl-1'-methyl-5-methoxy-2-oxospiro(3H-indole-3,3'-pyrrolidine) (222533-59-7)

Guidance literature:

Multi-step reaction with 13 steps

1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / Ambient temperature

2: 1.) n-BuLi / 1.) toluene, ether, hexane, -78 -> 0 deg C, 2.) toluene, ether, hexane, -78 -> -10 deg C

3: 95 percent / HCl / methanol

4: 97 percent / NaBH₄ / dioxane; methanol / 1 h

5: 1.) NaH / 1.) DMF, mineral oil, room temperature, 30 min, 2.) DMF, mineral oil, 0 deg C, 5 h

6: 80 percent / sodium nitrite, acetic acid / dimethylsulfoxide / 8 h / 37 °C

7: 1.) triethylamine, diphenylphosphoryl azide / 1.) toluene, reflux, 2 h, 2.) toluene, reflux, 12 h

8: 1.) ozone, 2.) dimethyl sulfide / 1.) ethanol, -78 deg C, 2.) ethanol, room temperature, overnight

9: NaBH₄ / methanol / 1 h

10: triethylamine / CH₂Cl₂ / 1 h / 0 °C

11: NaH / tetrahydrofuran; paraffin / 10 h / Ambient temperature

12: hydrogen / Pd/C / methanol / 8 h / Ambient temperature

13: 1.) NaCNBH₃, 2.) acetic acid / 1.) acetonitrile, water, 15 min, 2.) acetonitrile, water, 1 h

With 2,6-dimethylpyridine; hydrogenchloride; sodium tetrahydroborate; n-butyllithium; dimethylsulfide; diphenylphosphoranyl azide; hydrogen; sodium hydride; sodium cyanoborohydride; ozone; acetic acid; triethylamine; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; dimethyl sulfoxide; paraffin;

DOI:10.1021/jo981577q

upstream raw materials:

5-methoxyindolin-2-one

prenyl bromide

Downstream raw materials:

1-benzyl-5-methoxy-1'-methyl-1H-spiro[indole-3,3'-pyrrolidin]-2-one

(R)-1-benzyl-1'-methyl-5-methoxy-2-oxospiro(3H-indole-3,3'-pyrrolidine)

(S)-1-benzyl-3-(3-methylbut-2-enyl)-5-methoxy-3-(2-nitroethyl)-2-oxindole

(R)-1-benzyl-1'-ethoxycarbonyl-5-methoxy-2-oxospiro(3H-indole-3,3'-pyrrolidine)

Refernces