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

HRID 356948노트

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HRID 356948 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 21187944Methyl 3-cyclopentyloxy-4-(methylthio)benzoate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-2c2296cec3ca4fbd8cdd0f70c5e15e2b
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05840724

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