Sodium hydride → 3-(2-Chloro-phenylsulfanyl)-cyclopentanecarboxylic acid methyl ester

HRID 1367472Notes

Reaction equation

HRID 1367472 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[H-].[Na+].[CH3:11][O:12][C:13]([CH:15]1[CH2:19][CH2:18][CH:17](OS(C)(=O)=O)[CH2:16]1)=[O:14]>C1COCC1>[CH3:11][O:12][C:13]([CH:15]1[CH2:19][CH2:18][CH:17]([S:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[CH2:16]1)=[O:14]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 80599o-ChlorothiophenolHCID 205054773-(Methoxycarbonyl)cyclopentyl methanesulfonate

Product 1

HCID 669185443-(2-Chloro-phenylsulfanyl)-cyclopentanecarboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-chlorothiophenol (0.19 g, 1.5 eq) in THF (6.0 mL) was treated with NaH (60% dispersion in mineral oil, 0.05 g, 1.5 eq). The resulting solution was stirred at RT for 30 min. A solution of 3-methanesulfonyloxy-cyclopentanecarboxylic acid methyl ester (0.20 g, 1.0 eq) in THF (2.0 mL) was then added dropwise. The mixture was warmed at 50° C. and stirred for 3 h. The mixture was partitioned between 1N sodium bicarbonate and ethyl acetate. The combined organic phases were dried over sodium sulfate and evaporated. The title compound was obtained as a colorless oil (0.24 g, 98%) and was used without further purification in the next step. MS (ESI): m/z=271.2 [M+H]+.

Workup

  1. temperatureThe mixture was warmed at 50° C.
  2. stirringstirred for 3 h
  3. customThe mixture was partitioned between 1N sodium bicarbonate and ethyl acetate
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-1cca34fc6500435a9c2a892dee461348
Source dataset
uspto-grants-2011_02
Patent number
US07893099B2

Reaction notes

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