Acetic Anhydride → 1-Acetyl-7-(benzyloxy)-1H-indole-4-carbaldehyde

HRID 1762963Notes

Reaction equation

HRID 1762963 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:18]=[O:19])=[C:13]2[C:17]=1[NH:16][CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:27](OC(=O)C)(=[O:29])[CH3:28]>CN(C)C1C=CN=CC=1.ClCCl>[C:27]([N:16]1[C:17]2[C:13](=[C:12]([CH:18]=[O:19])[CH:11]=[CH:10][C:9]=2[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:14]=[CH:15]1)(=[O:29])[CH3:28]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 132434867-(Benzyloxy)-1H-indole-4-carbaldehyde

Product 1

HCID 132434871-Acetyl-7-(benzyloxy)-1H-indole-4-carbaldehyde

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

500 mg of 7-benzyloxy-4-formylindole is combined with 50 mg of 4-dimethylaminopyridine, 0.7 ml of triethylamine, 0.5 ml of acetic anhydride, and 10 ml of dichloromethane and agitated for 24 hours at room temperature. The reaction mixture is then diluted with 50 ml of dichloromethane, washed with concentrated sodium bicarbonate solution; the organic phase is dried and concentrated. The residue is recrystallized from isopropanol, thus obtaining 400 mg of 1-acetyl-7-benzyloxy-4-formylindole, mp 77°-78° C.

Workup

  1. washwashed with concentrated sodium bicarbonate solution
  2. customthe organic phase is dried
  3. concentrationconcentrated
  4. customThe residue is recrystallized from isopropanol

Sources & evidence

ORD record
ord-1271ca2d44dc4500b5e5364331e39618
Source dataset
uspto-grants-1989_05
Patent number
US04835175

Reaction notes

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