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

HRID 1296217

反応式

HRID 1296217 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+]>CN(C)C=O.[C]=O.C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.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

8

反応物 2

HCID 2723810Sodium FormateHCID 22926030Tert-butyl (5-bromo-2-methoxybenzyl)carbamate

生成物 1

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

試薬・触媒・溶媒 5

HCID 11776Triphenylphosphine触媒HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒HCID 178418416HCID 178418416、化合物溶媒

実験手順

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

後処理

  1. washwashed with water and saturated sodium bicarbonate water
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated
  4. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-04a0c5bca7cd4ea2a1e72ff93846ae5a
出典データセット
uspto-grants-2007_07
特許番号
US07244861B2

関連ノート

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