Dimethylformamide → 4-(Tert-butyldiphenylsilyloxymethyl)-3-methylbenzaldehyde

HRID 584213노트

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HRID 584213 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][Si:10]([C:23]([CH3:26])([CH3:25])[CH3:24])([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:4]([CH3:27])[CH:3]=1.C([Li])CCC.CN(C)[CH:35]=[O:36].[Cl-].[NH4+]>O1CCCC1.CCCCCC>[Si:10]([O:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([CH:35]=[O:36])=[CH:3][C:4]=1[CH3:27])([C:23]([CH3:26])([CH3:25])[CH3:24])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 223426891-Bromo-4-(tert-butyldiphenylsilyloxymethyl)-3-methylbenzeneHCID 178418339Butyllithium

생성물 1

HCID 223429234-(Tert-butyldiphenylsilyloxymethyl)-3-methylbenzaldehyde

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

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온도
-78 °C

실험 절차

To a stirred solution of 1-bromo-4-(tert-butyldiphenylsilyloxymethyl)-3-methylbenzene (2.19 g) in tetrahydrofuran (30 ml) was added 1.6 M butyllithium in hexane (4.69 ml) by syringe under nitrogen atmosphere at −78° C. After 30 minutes of stirring at −78° C., N,N-dimethylformamide (1.16 ml) was added to the solution at −78° C. and then the mixture was allowed to warm to 5° C. over 1.5 hours. Saturated ammonium chloride solution (10 ml) was added to the mixture and the organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The combined extract was washed with water, dried over magnesium sulfate, and concentrated under reduced pressure to give 4-(tert-butyldiphenylsilyloxymethyl)-3-methylbenzaldehyde (1.90 g) as a colorless oil.

후처리

  1. temperatureto warm to 5° C. over 1.5 hours
  2. customthe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. extractionThe combined extract
  5. washwas washed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-dbd503d70030487b83e01f727d4a039e
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06924278B2

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