Acetic Anhydride → O-acetyl-1-(3,4-dimethoxyphenyl)-2-nitro-6-cyano-6-(i-propyl)-6-(3,4-dimethoxyphenyl)hexan-3-ol

HRID 979377Notes

Reaction equation

HRID 979377 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH:12]([N+:33]([O-:35])=[O:34])[CH:13]([OH:32])[CH2:14][CH2:15][C:16]([C:30]#[N:31])([CH:27]([CH3:29])[CH3:28])[C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[CH:18]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[C:36](OC(=O)C)(=[O:38])[CH3:37]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:36]([O:32][CH:13]([CH2:14][CH2:15][C:16]([C:30]#[N:31])([CH:27]([CH3:29])[CH3:28])[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[CH:18]=1)[CH:12]([N+:33]([O-:35])=[O:34])[CH2:11][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)(=[O:38])[CH3:37]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 137457541-(3,4-Dimethoxyphenyl)-2-nitro-6-cyano-6-(prop-2-yl)-6-(3,4-dimethoxyphenyl)hexan-3-ol

Product 1

HCID 13745755O-acetyl-1-(3,4-dimethoxyphenyl)-2-nitro-6-cyano-6-(i-propyl)-6-(3,4-dimethoxyphenyl)hexan-3-ol

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(3,4-dimethoxyphenyl)-2-nitro-6-cyano-6-(i-propyl)-6-(3,4-dimethoxyphenyl)hexan-3-ol (8, 75 g, 0.154 mol), 4-dimethylaminopyridine ("DMAP," 1.5 g, Aldrich), and acetic anhydride (23 mL) in CH2Cl2 (700 mL) was heated at reflux for 40 minutes to yield 1-(3,4-dimethoxyphenyl)-2-nitro-3-acetoxy-6-cyano-6-(i-propyl)-6-(3,4-dimethoxyphenyl)hexane (9), which was used in the next step without isolation.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 40 minutes

Sources & evidence

ORD record
ord-9187cc3bab614a949c1b7cb7c1465bf2
Source dataset
uspto-grants-1987_05
Patent number
US04667038

Reaction notes

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