Diethyl Ether → Acetic acid, (phenylthio)-, ethyl ester

HRID 2053598Notes

Reaction equation

HRID 2053598 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].CCOCC>CN(C=O)C>[CH2:19]([O:18][C:16](=[O:17])[CH2:15][S:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:20]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 7748Ethyl bromoacetateHCID 7969ThiophenolHCID 11430Potassium Carbonate

Product 1

HCID 97312Acetic acid, (phenylthio)-, ethyl esterYield 89.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of thiophenol (1 mL, 9.7 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 1.71 g of the product 400. 1H NMR (CDCl3) δ 7.41 (d, 2H), 7.33-7.2 (m, 4H), 4.16 (q, 2H), 3.63 (s, 2H), 1.22 (t, 3H); MS: m/z 196 (M++1).

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-d2a831cb650349ef99314ae722e8c6bb
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Reaction notes

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