Diethyl Ether → Ethyl 2-(Benzylsulfanyl)acetate

HRID 2053599Notes

Reaction equation

HRID 2053599 reaction equation
[CH2:1]([SH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].CCOCC>CN(C=O)C>[CH2:20]([O:19][C:17](=[O:18])[CH2:16][S:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:21]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 7509Benzyl mercaptanHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate

Product 1

HCID 3344750Ethyl 2-(Benzylsulfanyl)acetateYield 49.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of benzyl mercaptan (1.18 mL, 10.0 mmol) in DMF (20 mL) is added potassium carbonate (1.51 g, 10.9 mmol) and ethyl bromoacetate (1.17 mL, 10.6 mmol), and the mixture is stirred at RT for 25 min. Et2O is added, and the mixture is washed with water, brine, then dried (MgSO4), and filtered. The filtrate is evaporated, and the residue is vacuum distilled (130-140° C.) to give 1.05 g of the product 402.

Workup

  1. washthe mixture is washed with water, brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customThe filtrate is evaporated
  5. distillationdistilled (130-140° C.)

Sources & evidence

ORD record
ord-92da71d1e5b14ab486c7943adb517ed4
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Reaction notes

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