Water → HCID 54091903, compound

HRID 2396115Notes

Reaction equation

HRID 2396115 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[SH:11]CC(OCC)=O.C(=O)([O-])[O-].[K+].[K+].O.[O:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1>>[CH2:2]([CH2:27][C:26]([O:25][CH2:29][CH3:28])=[S:11])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4]

Participants

6

Reactant 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 107572-ChloroacetophenoneHCID 11430Potassium CarbonateHCID 12185Ethyl Thioglycolate

Product 1

HCID 54091903HCID 54091903, compound

Procedure

Part A. A solution of 2-chloroacetophenone (Aldrich, 14.1 g, 91.2 mmol), ethyl 2-mercaptoacetate (Aldrich, 10.0 mL, 91.2 mmol), and potassium carbonate (13.9 g, 100 mmol) in tetrahydrofuran (200 mL) was stirred at ambient temperature for 10 hours. The mixture was poured into water (400 mL), and extracted with methylene chloride (2×400 mL). The extracts were combined, dried over anhydrous magnesium sulfate, filtered and evaporated. The residual oil was separated by flash chromatography (1:4 ethyl acetate-hexane) to afford the product, ethyl 2-phenacylthioacetate, as an oil (16.1 g, 67.7 mmol, 74%). 1H NMR (CDCl3): δ 7.97 (2H, dd, J=8.0, 1.5 Hz); 7.62 (1H, tt, J=5.1, 1.4 Hz); 7.48 (2H, t, J=7.7 Hz); 4.19 (2H, q, J=7.3 Hz); 4.04 (2H, s); 3.33 (2H, s); 1.27 (3H, t, J=7.3 Hz). Mass spectrum (NH3 -CI/DDIP): m/z 256 (100%); 240 (6%);239 (42%); 210 (1%); 193 (1%).

Workup

  1. extractionextracted with methylene chloride (2×400 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residual oil was separated by flash chromatography (1:4 ethyl acetate-hexane)

Sources & evidence

ORD record
ord-5202007eb3954c56b878f010b9b0ae22
Source dataset
uspto-grants-1996_02
Patent number
US05491152

Reaction notes

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