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

HRID 1584932Notes

Reaction equation

HRID 1584932 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  1. stirringstirred at 60° C. for 3 hours
  2. concentrationconcentrated
  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)

Sources & evidence

ORD record
ord-ef02ca2df1c3450fab91d4178bfc0290
Source dataset
uspto-grants-1999_08
Patent number
US05935978

Reaction notes

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