Dimethylformamide → HCID 20077568, 화합물

HRID 1655077노트

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HRID 1655077 반응식
[Si:1]([C:8]1[S:9][CH:10]=[CH:11][N:12]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([Li])CCC.CN(C)[CH:20]=[O:21].[Cl-].[NH4+]>CCOCC>[Si:1]([C:8]1[S:9][C:10]([CH:20]=[O:21])=[CH:11][N:12]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 104653742-(tert-Butyldimethylsilyl)thiazoleHCID 178418339Butyllithium

생성물 1

HCID 20077568HCID 20077568, 화합물수율 69%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

반응 조건

온도
-40 °C

실험 절차

A solution of compound Q (40 g) in ether (100 ml) was added dropwise to a solution of n-butyllithium (1.6M solution in hexane, 138 ml) in ether (300 ml) at -70° C. under an atmosphere of argon. The mixture was stirred for 1 hour at this temperature and then N,N-dimethylformamide (30 ml) was added dropwise. The mixture was stirred for 30 minutes at -70° C., then warmed to -40° C. Excess saturated aqueous ammonium chloride solution was added and the mixture allowed to warm to ambient temperature. The layers were separated and the aqueous phase extracted three times with ether. The organic phases were combined, dried (MgSO4), and concentrated. The residue was purified by column chromatography, eluting with 25% ethyl acetate/hexane (v/v), to give 2-tert-butyldimethylsilylthiazole-5-carboxaldehyde (R) (31 g, 69% yield) as an oil; NMR: 0.32(6H,s), 0.89(9H,s), 8.55(1H,s), 10.0(1H,s).

후처리

  1. stirringThe mixture was stirred for 30 minutes at -70° C.
  2. temperatureto warm to ambient temperature
  3. customThe layers were separated
  4. extractionthe aqueous phase extracted three times with ether
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography
  8. washeluting with 25% ethyl acetate/hexane (v/v)

출처 및 근거

ORD 기록
ord-9bc15ac4859a44779678ad779b214c40
출처 데이터셋
uspto-grants-1995_04
특허 번호
US05410064

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