1-Bromo-1-methylcyclopropane → Cyclopropylmethyl-p-toluenethiosulfonate

HRID 1720074ノート

反応式

HRID 1720074 の反応式
[CH3:1][C:2]1(Br)[CH2:4][CH2:3]1.[S:6]([C:10]1[CH:16]=[CH:15][C:13]([CH3:14])=[CH:12][CH:11]=1)([O-:9])(=[O:8])=[S:7].[K+]>C(O)C>[CH:4]1([CH2:3][O:9][S:6]([C:10]2[CH:16]=[CH:15][C:13]([CH3:14])=[CH:12][CH:11]=2)(=[S:7])=[O:8])[CH2:2][CH2:1]1

参加物

4

反応物 2

HCID 148649461-Bromo-1-methylcyclopropaneHCID 23662126Benzenesulfonothioic acid, 4-methyl-, potassium salt (1:1)

生成物 1

HCID 86749376Cyclopropylmethyl-p-toluenethiosulfonate収率 72.5%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
90 °C

実験手順

To a solution of methylcyclopropyl bromide (4.00 g, 29.6 mmol) in ethanol (20.0 mL) was added potassium thiotosylate (10.0 g, 44.4 mmol) and the mixture heated to 90° C. for 10 h. The mixture was then quenched into a 1:1 mixture of H2O (50.0 mL) and diethyl ether (50.0 mL). The layers were separated and the organic layer washed with brine (50.0 mL). The organic layer was then dried with MgSO4 and concentrated in vacuo to yield the title compound as a solid (5.2 g, m.p. 46°-48° C.). 'H NMR (400 MHz, CDCl3) δ 7.816 (d, 2H, J=8.8 Hz), 7.308 (d, 2H, J =8.8 Hz), 2.945 (d, 2H, J=7.6 Hz), 2.451 (s, 3H), 1.010-0.933 (m, 1H), 0.592-0.545 (m, 2H), 0.236-0.197 (m, 2H).

後処理

  1. customThe mixture was then quenched into a 1:1 mixture of H2O (50.0 mL) and diethyl ether (50.0 mL)
  2. customThe layers were separated
  3. washthe organic layer washed with brine (50.0 mL)
  4. dry with materialThe organic layer was then dried with MgSO4
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-5a56bb9c9d3942f29a2ffffb13ce6f72
出典データセット
uspto-grants-1996_04
特許番号
US05504104

反応ノート

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