Ammonium Chloride → 5-[2-(1,3-Difluoro-2-methylpropan-2-yl)oxiran-2-yl]-1,3-thiazole

HRID 2092942ノート

反応式

HRID 2092942 の反応式
C[Si](C)(C)[C:3]1[S:4][CH:5]=[CH:6][N:7]=1.C([Li])CCC.Br[CH2:16][C:17](=[O:24])[C:18]([CH2:22][F:23])([CH3:21])[CH2:19][F:20].[Cl-].[NH4+]>C(OCC)C>[F:20][CH2:19][C:18]([C:17]1([C:5]2[S:4][CH:3]=[N:7][CH:6]=2)[CH2:16][O:24]1)([CH3:21])[CH2:22][F:23]

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 5884532-TrimethylsilylthiazoleHCID 130194343,3-Bisfluoromethyl-1-bromo-butan-2-oneHCID 178418339Butyllithium

生成物 1

HCID 866617115-[2-(1,3-Difluoro-2-methylpropan-2-yl)oxiran-2-yl]-1,3-thiazole

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

To 2.00 g (12.7 mmol) of 2-trimethylsilyl-1,3-thiazole dissolved in 20 ml of diethyl ether were added, at −78° C. under an argon atmosphere, 5.1 ml (2.5 M, 12.7 mmol) of n-butyllithium, and the reaction mixture was stirred at −78° C. for 20 min. Then 2.73 g (12.7 mmol) of 1-bromo-4-fluoro-3-(fluoromethyl)-3-methylbutan-2-one were added and the reaction mixture was gradually warmed to room temperature. After addition of saturated aqueous ammonium chloride solution, the phases were separated and the aqueous phase was extracted with diethyl ether. The combined organic phases were dried over sodium sulphate, filtered and concentrated. The crude product was then purified by column chromatography (5:1 cyclohexane/ethyl acetate). This gave 2.39 g (86%) of the desired product.

後処理

  1. additionwere added, at −78° C. under an argon atmosphere
  2. customthe phases were separated
  3. extractionthe aqueous phase was extracted with diethyl ether
  4. dry with materialThe combined organic phases were dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was then purified by column chromatography (5:1 cyclohexane/ethyl acetate)

出典と根拠

ORDレコード
ord-117fbc51cf844377a02838d13a8c49cb
出典データセット
uspto-grants-2013_05
特許番号
US08440836B2

反応ノート

読み込み中…