Acetic Anhydride → HCID 22414908, compound

HRID 1721428Notes

Reaction equation

HRID 1721428 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[CH2:8]([C:11]1C(O)=[C:13]2[C:17](=[C:18]([CH3:20])[CH:19]=1)[N:16]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:15](=[O:28])[C:14]2(C)[CH3:29])[CH:9]=[CH2:10]>N1C=CC=CC=1>[C:5]([O:4][C:1]1[C:11]([CH2:8][CH:9]=[CH2:10])=[CH:19][C:18]([CH3:20])=[C:17]2[C:2]=1[C:14]([CH3:29])([CH3:13])[C:15](=[O:28])[N:16]2[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 22414850HCID 22414850, compound

Product 1

HCID 22414908HCID 22414908, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2.5 g (50.9 mmol) of acetic anhydride was added to a solution of 8.2 g (25.5 mmol) of 5-allyl-1-benzyl-2,3-dihydro-4-hydroxy-3,3,7-trimethyl-1H-indol-2-one and 250 mg (2.0 mmol) of N,N-dimethylaminopyridine in 80 ml of pyridine under cooling with ice, and the mixture was stirred overnight at room temperature. The reaction mixture was poured into ice water, washed with 10% hydrochloric acid, washed with water, and dried. The solvent was evaporated and the residue was purified by column chromatography (silica gel, 5:1 mixture of n-hexane and ethyl acetate) to obtain 8.0 g (yield, 85.2%) of colorless needles of the title compound.

Workup

  1. temperatureunder cooling with ice
  2. washwashed with 10% hydrochloric acid
  3. washwashed with water
  4. customdried
  5. customThe solvent was evaporated
  6. customthe residue was purified by column chromatography (silica gel, 5:1 mixture of n-hexane and ethyl acetate)
  7. customto obtain

Sources & evidence

ORD record
ord-565f15f6786b44f1bf944e0b0aeef040
Source dataset
uspto-grants-1996_04
Patent number
US05510366

Reaction notes

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