Triethylamine → 2-(4-Methoxycarbonylphenylthio)-2-tert.butoxycarbonylcyclohexanone

HRID 1588421ノート

反応式

HRID 1588421 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11]Cl)=[CH:7][CH:6]=1)=[O:4].[C:13]([O:17][C:18]([CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][C:21]1=[O:26])=[O:19])([CH3:16])([CH3:15])[CH3:14].C(N(CC)CC)C>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11][C:20]2([C:18]([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:19])[CH2:25][CH2:24][CH2:23][CH2:22][C:21]2=[O:26])=[CH:7][CH:6]=1)=[O:4]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 12431017tert-Butyl 2-oxocyclohexane-1-carboxylateHCID 15584701Methyl 4-(chlorosulfanyl)benzoate

生成物 1

HCID 197556512-(4-Methoxycarbonylphenylthio)-2-tert.butoxycarbonylcyclohexanone収率 56.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

A solution 10.8 g (53.2 mmol) of 4-methoxycarbonylphenylsulphenic acid chloride in 20 ml of methylene chloride (analytically pure) is added dropwise to a solution of 11.4 g (57 mmol) of 2-tert.butoxycarbonylcyclohexanone and 7.5 g (75 mmol) of triethylamine in 150 ml of methylene chloride. When the dropwise addition has ended the mixture is subsequently stirred for 15 mins. and is then diluted with methylene chloride and the organic phase is washed with 2N sulphuric acid and a saturated bicarbonate solution, dried with sodium sulphate and concentrated by evaporation. 20.5 g of a crude product are thus obtained, which is chromatographed on 2 kg of silica gel (Merck Si 60, 0.04-0.063 nm) using petroleum ether/ether 8:20 as the mobile solvent. A fraction is thus obtained which, after being concentrated by evaporation, yields 11 g of a solid product.

後処理

  1. additionWhen the dropwise addition
  2. washthe organic phase is washed with 2N sulphuric acid
  3. dry with materiala saturated bicarbonate solution, dried with sodium sulphate
  4. concentrationconcentrated by evaporation
  5. custom20.5 g of a crude product are thus obtained
  6. customwhich is chromatographed on 2 kg of silica gel (Merck Si 60, 0.04-0.063 nm)
  7. customA fraction is thus obtained which
  8. concentrationafter being concentrated by evaporation

出典と根拠

ORDレコード
ord-962a509f4aae49d0a3f4c58be3129965
出典データセット
uspto-grants-1993_06
特許番号
US05221760

反応ノート

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