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

HRID 1816583

反応式

HRID 1816583 の反応式
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]

参加物

7

反応物 3

HCID 2723810Sodium FormateHCID 22926030Tert-butyl (5-bromo-2-methoxybenzyl)carbamateHCID 178418416HCID 178418416、化合物

生成物 1

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

試薬・触媒・溶媒 3

HCID 11776Triphenylphosphine触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-2a1a9a721a2944d49cd57c440706ca11
出典データセット
uspto-grants-2005_04
特許番号
US06884821B1

関連ノート

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