Diethyl Ether → Ethyl 2-(Benzylsulfanyl)acetate
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
Product 1
Reagents, catalysts & solvents 1
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
- washthe mixture is washed with water, brine
- dry with materialdried (MgSO4)
- filtrationfiltered
- customThe filtrate is evaporated
- distillationdistilled (130-140° C.)
Sources & evidence
- ORD record
- ord-b23c6536424c4e7d8c34c22f26f46f35
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07741493B2
Reaction notes
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