Benzyl mercaptan → HCID 68843484, compound

HRID 660746Notes

Reaction equation

HRID 660746 reaction equation
[H-].[Na+].[CH2:3]([SH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17](=[O:19])[CH3:18]>CN(C=O)C>[CH2:3]([S:10][CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17](=[O:19])[CH3:18])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 7509Benzyl mercaptanHCID 24758Sodium hydrideHCID 784911-Butanol, 4-bromo-, 1-acetate

Product 1

HCID 68843484HCID 68843484, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of NaH (0.45 g, 60% in mineral oil, 11.1 mmol) in DMF (5 mL) is added benzylmercaptan (1.43 mL, 11.03 mmol) and the resulting yellow solution is stirred at RT for 30 min. The mixture is cooled to 0° C. then acetic acid 4-bromobutyl ester (2.2 g, 11.2 mmol) is added dropwise (exothermic). The mixture is allowed to warm to RT and is quenched with 1N HCl (35 mL). The mixture is extracted with MTBE and the organic phase is dried over magnesium sulfate. The solvent is removed under reduced pressure and the residue is purified by flash chromatography using EtOAc/hexane (4:1) as eluent to give the title compound as an oil.

Workup

  1. temperatureThe mixture is cooled to 0° C.
  2. temperatureto warm to RT
  3. customis quenched with 1N HCl (35 mL)
  4. extractionThe mixture is extracted with MTBE
  5. dry with materialthe organic phase is dried over magnesium sulfate
  6. customThe solvent is removed under reduced pressure
  7. customthe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-2dc6cedf2f1143d8b157861c07cd7c0c
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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