Sodium Formate → Tert-butyl (5-formyl-2-methoxybenzyl)carbamate

HRID 1816583

반응식

HRID 1816583 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([O:17][CH3:18])=[C:6]([CH:16]=1)[CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12].[CH:19]([O-])=[O:20].[Na+].[C]=O>CN(C)C=O.C(OCC)(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:19]([C:2]1[CH:3]=[CH:4][C:5]([O:17][CH3:18])=[C:6]([CH:16]=1)[CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:20]

참가 물질

7

반응물 3

HCID 2723810Sodium FormateHCID 22926030Tert-butyl (5-bromo-2-methoxybenzyl)carbamateHCID 178418416HCID 178418416, 화합물

생성물 1

HCID 22493931Tert-butyl (5-formyl-2-methoxybenzyl)carbamate수율 75.1%

시약·촉매·용매 3

HCID 11776Triphenylphosphine촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

1.015 g of tertiary butyl N-(5-bromo-2-methoxybenzyl)carbamate, 45 mg of dichlorobis(triphenylphosphine) palladium (II), 330 mg of sodium formate and 17 mg of triphenyl phosphine were dissolved in anhydrous N,N-dimethylformamide and stirred at 110° C. for 2 hours in a carbon monoxide atmosphere. The reaction mixture was diluted with ethyl acetate, and successively washed with water and saturated aqueous sodium bicarbonate. The organic layer was dried over anhydrous magnesium sulfate and the solvent was evapoarated. The residue was purified by silica gel column chromatography, and from fractions eluted with hexane-ethyl acetate (3:1), 640 mg of tertiary butyl N-(5-formyl-2-methoxybenzyl)carbamate was obtained.

후처리

  1. washsuccessively washed with water and saturated aqueous sodium bicarbonate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customThe residue was purified by silica gel column chromatography
  4. washfrom fractions eluted with hexane-ethyl acetate (3:1)

출처 및 근거

ORD 기록
ord-2a1a9a721a2944d49cd57c440706ca11
출처 데이터셋
uspto-grants-2005_04
특허 번호
US06884821B1

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