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

HRID 356948ノート

反応式

HRID 356948 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

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; that is prepared as described in Reference Example 53) in dry dimethyl-formamide (40 mL) is treated with sodium hydride (0.44 g of a 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. customthat is prepared
  2. stirringstirred at 60° C. for 3 hours
  3. concentrationconcentrated
  4. customThe resulting residue is partitioned between dichloromethane (50 mL) and water (50 mL)
  5. extractionthe aqueous layer is extracted with dichloromethane (50 mL)
  6. customthe combined organic layers are dried
  7. concentrationconcentrated
  8. customto give a red oil
  9. washeluting with a mixture of diethyl ether and pentane (1:9 v/v)

出典と根拠

ORDレコード
ord-2c2296cec3ca4fbd8cdd0f70c5e15e2b
出典データセット
uspto-grants-1998_11
特許番号
US05840724

反応ノート

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