Acetic Anhydride → HCID 70043507, compound

HRID 257740Notes

Reaction equation

HRID 257740 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][CH2:12][OH:13])=[CH:2]1.[Si:14]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15].[C:29](OC(=O)C)(=[O:31])[CH3:30]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:29]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][CH2:12][OH:13])=[CH:2]1)(=[O:31])[CH3:30].[Si:14]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:23])[CH3:24])([C:17]([CH3:19])([CH3:20])[CH3:18])([CH3:16])[CH3:15]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 70046065HCID 70046065, compound

Product 1

HCID 70043507HCID 70043507, compoundYield 67.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of the indole 29 (29 g, 86 mmol), CH2Cl2 (450 mL), 1,8-diazobicyclo[5.4.0]undec-7-ene (38 mL, 0.26 mol), 4-dimethylaminopyridine (1.0 g, 8.5 mmol), and acetic anhydride (32 mL, 0.34 mol) was stirred for 1 week at ambient temperature. The reaction mixture was concentrated and then diluted with ether. The ether was then washed with H2O, 5% KHSO4 and brine, dried (MgSO4), and concentrated. Flash chromatography (silica, 5% ethyl acetate/hexanes) gave the acylated product 30 (27 g) as a yellow oil. TLC Rf=0.56 (20% ethyl acetate/hexanes).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with ether
  3. washThe ether was then washed with H2O, 5% KHSO4 and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-32331fcf5bbe4b349a4577096bb0ea3c
Source dataset
uspto-grants-1993_11
Patent number
US05264420

Reaction notes

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