Bromocyclopentane → Methyl 3-cyclopentyloxy-4-(methylthio)benzoate

HRID 1383503ノート

反応式

HRID 1383503 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[S:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6].[H-].[Na+].[CH:16]1(Br)[CH2:20][CH2:19][CH2:18][CH2:17]1>CN(C)C=O>[CH:16]1([O:1][C:2]2[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=2[S:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6])[CH2:20][CH2:19][CH2:18][CH2:17]1

参加物

5

反応物 3

HCID 8728BromocyclopentaneHCID 24758Sodium hydrideHCID 21187893Methyl 3-hydroxy-4-(methylthio)benzoate

生成物 1

HCID 21187944Methyl 3-cyclopentyloxy-4-(methylthio)benzoate収率 71.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A stirred solution of methyl 3-hydroxy-4(methylthio)benzoate (1.98 g) in dry dimethylformamide (40 mL) is treated with sodium hydride (0.44 g; 60% dispersion in mineral oil; 11 mmol) and the solution is stirred for a further 25 minutes. The reaction mixture is treated with cyclopentyl bromide (1.64 g), stirred at 60° C. for 3 hours. and then concentrated. The resulting residue is partitioned between dichloromethane (50 mL) and water (50 mL), the aqueous layer is extracted with dichloromethane (50 mL), and the combined organic layers are dried and concentrated, to give a red oil. The oil is subjected to flash chromatography, eluting with a mixture of diethyl ether and pentane (1:9 v/v), to give methyl 3-cyclopentyloxy-4-(methylthio)benzoate (1.9 g), m.p. 53-55° C.

後処理

  1. stirringstirred at 60° C. for 3 hours
  2. concentrationand then concentrated
  3. customThe resulting residue is partitioned between dichloromethane (50 mL) and water (50 mL)
  4. extractionthe aqueous layer is extracted with dichloromethane (50 mL)
  5. customthe combined organic layers are dried
  6. concentrationconcentrated
  7. customto give a red oil
  8. washeluting with a mixture of diethyl ether and pentane (1:9 v/v)

出典と根拠

ORDレコード
ord-07e91960a00a4e9cb461921dd423158f
出典データセット
uspto-grants-2001_07
特許番号
US06255326B1

反応ノート

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