Hydrochloric Acid → HCID 13693403、化合物

HRID 981254ノート

反応式

HRID 981254 の反応式
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:12])[CH2:10][CH3:11])=[CH:5][CH:4]=1.Br[CH2:14][C:15]([O:17][CH3:18])=[O:16].Cl>C1(C)C=CC=CC=1.C1COCC1>[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:12])[CH:10]([CH3:11])[CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:5][CH:4]=1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 60984Methyl bromoacetateHCID 8211711-[4-(Methylthio)phenyl]-1-propanone

生成物 1

HCID 13693403HCID 13693403、化合物

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
-78 °C

実験手順

To a solution of potassium hexamethylsilazane (0.158 mole) in toluene (254 ml) and THF (160 ml) at -78° C. was added dropwise the ketone from Step A of this Example (25.8 g) in THF (90 ml). The reaction mixture was stirred 30 minutes at -78° C. Methyl bromoacetate (16.2 ml) in THF (25 ml) was added dropwise. After stirring 1.5 hours at -78° C. the reaction mixture was poured into 1N HCl (400 ml). The organic layer was separated and the aqueous layer was further extracted with ethyl acetate. The combined organic layers were washed with water, dried over Na2SO4 and evaporated to give a yellow oil which was purified on a flash silica gel column (1 kg) using hexane/EtOAc (10:2) as eluant to give the title compound as an oil.

後処理

  1. stirringAfter stirring 1.5 hours at -78° C. the reaction mixture
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was further extracted with ethyl acetate
  4. washThe combined organic layers were washed with water
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customto give a yellow oil which
  8. customwas purified on a flash silica gel column (1 kg)

出典と根拠

ORDレコード
ord-497c5b9182ea41329cb5c39fc4e745e9
出典データセット
uspto-grants-1991_02
特許番号
US04990526

反応ノート

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