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

HRID 613044ノート

反応式

HRID 613044 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.). 1H NMR (400 MHz, CDCl3) δ7.816 (d, 2 H, J=8.8 Hz), 7.308 (d, 2 H, J =8.8 Hz), 2.945 (d, 2 H, J=7.6 Hz), 2.451 (s, 3 H), 1.010-0.933 (m, 1 H), 0.592-0.545 (m, 2 H), 0.236-0.197 (m, 2 H).

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-e3f4040f41dd4b2aaee17f7beebd2ad3
出典データセット
uspto-grants-1999_12
特許番号
US06005103

反応ノート

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