Diethyl Ether → Ethyl 2-(Benzylsulfanyl)acetate

HRID 18808

Reaction equation

HRID 18808 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-b23c6536424c4e7d8c34c22f26f46f35
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Linked notes

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