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

HRID 1383531Notes

Reaction equation

HRID 1383531 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)benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-d520f7babe904b18899c7a87a0cb8e86
Source dataset
uspto-grants-2001_07
Patent number
US06255326B1

Reaction notes

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