Ethyl bromoacetate → HCID 52145790, compound

HRID 1912945Notes

Reaction equation

HRID 1912945 reaction equation
C([O-])([O-])=O.[K+].[K+].Br[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10].[CH:14]1([SH:19])[CH2:18][CH2:17][CH2:16][CH2:15]1>CN(C=O)C.O>[CH:14]1([S:19][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 15510Cyclopentanethiol

Product 1

HCID 52145790HCID 52145790, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

Solid K2CO3 (9.01 g, 65.2 mmol) was added to a stirring solution of ethyl bromoacetate (5.16 mL, 46.6 mmol) and cyclopentanethiol (4.97 mL, 46.6 mmol) in DMF (25 mL). The resulting suspension was warmed at 65° C. for 4 hours. The reaction mixture was cooled to room temperature, diluted with water (100 mL) and extracted with hexanes (3×50 mL). The combined extract was washed with saturated brine (30 mL) and concentrated under vacuum to provide the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 1.29 (t, J=7.1 Hz, 3H), 1.43-1.65 (m, 4H), 1.66-1.81 (m, 2H), 1.93-2.10 (m, 2H), 3.13-3.30 (m, 1H), 3.25 (s, 2H), 4.19 (q, J=7.1 Hz, 2H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with hexanes (3×50 mL)
  3. extractionThe combined extract
  4. washwas washed with saturated brine (30 mL)
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f19bc2caee9a47afa01ff9248d8631ad
Source dataset
uspto-grants-2013_12
Patent number
US08609669B2

Reaction notes

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