Water → HCID 22954344, compound

HRID 393452Notes

Reaction equation

HRID 393452 reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH2:10][CH2:11][CH2:12][CH2:13]Br)[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].[CH3:15][S-:16].[Na+].O>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1([CH2:10][CH2:11][CH2:12][CH2:13][S:16][CH3:15])[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 4378561Sodium methanethiolate2×HCID 229543431-(4-Bromobutyl)cyclopentanecarboxylic acid methyl ester

Product 1

HCID 22954344HCID 22954344, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(4-bromobutyl)cyclopentane carboxylic acid methyl ester (38 mmol, 10 g) in DMF (100 mL) was added sodium thiomethoxide (72.6 mmol, 5.09 g). After addition of sodium thiomethoxide, the reaction was exothermic and the mixture became a light brown cloudy solution. The mixture was stirred for 15 h at room temperature and was poured into water (200 mL). The organic compound was extracted with ether (2×150 mL). The combined extracts were washed with brine (150 mL) and dried over anhydrous magnesium sulfate. After filtration of the drying agent, the solution was concentrated under vacuum and the resulting residue was purified by silica gel column chromatography to afford 4.43 g (51%) of a colorless oil. LR MS (C12H22O2S): 230 (M+).

Workup

  1. extractionThe organic compound was extracted with ether (2×150 mL)
  2. washThe combined extracts were washed with brine (150 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationAfter filtration of the drying agent
  5. concentrationthe solution was concentrated under vacuum
  6. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3115b879014241d78163c1c7e446e875
Source dataset
uspto-grants-2004_10
Patent number
US06806365B2

Reaction notes

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