Dimethylformamide → HCID 20077568、化合物

HRID 1587799ノート

反応式

HRID 1587799 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 20077568HCID 20077568、化合物収率 69%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

反応条件

温度
-40 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-402f9b6437c14e318efceee9d8016d15
出典データセット
uspto-grants-1993_06
特許番号
US05219874

反応ノート

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