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

HRID 1296217노트

반응식

HRID 1296217 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+]>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]

참가 물질

8

반응물 2

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

생성물 1

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

시약·촉매·용매 5

HCID 11776Triphenylphosphine촉매HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매HCID 178418416HCID 178418416, 화합물용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-04a0c5bca7cd4ea2a1e72ff93846ae5a
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07244861B2

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