Potassium Carbonate → HCID 131729804, compound

HRID 1511513Notes

Reaction equation

HRID 1511513 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[O:9][CH3:10].C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20]>CN(C=O)C.O>[C:22]([O:21][C:19](=[O:20])[CH2:18][O:8][C:5]1[CH:6]=[CH:7][C:2]([I:1])=[C:3]([O:9][CH3:10])[CH:4]=1)([CH3:25])([CH3:24])[CH3:23]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 57671757HCID 57671757, compound

Product 1

HCID 131729804HCID 131729804, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Compound 1 (0.8 g, 3.19 mmol) was dissolved in dry DMF (30 ml). Dried potassium carbonate (1.32 g, 9.57 mmol) was added and the mixture was deaerated with argon. Tert-butyl bromoacetate (0.71 ml, 4.78 mmol) was added to the mixture and the reaction was stirred overnight at 70° C. The reaction mixture was cooled to room temperature and diluted with water (20 ml). The product was extracted with diethyl ether (3×50 ml) and dried over sodium sulphate. The product was purified by flash chromatography on silica gel using dichloromethane as an eluent. The yield was 1.1 g (96%). 1H NMR (CDCl3, 500 MHz): δ 7.66 (1H, d, J=8.5 Hz), 6.39 (1H, dd, J=8.5 Hz, 2.5 Hz), 6.34 (1H, d, J=2.5), 4.57 (2H, s), 3.79 (3H, s), 1.51 (9H, s).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionThe product was extracted with diethyl ether (3×50 ml)
  3. dry with materialdried over sodium sulphate
  4. customThe product was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-a78f97e7fd314dc2a9b63a7562eadb79
Source dataset
uspto-grants-2012_07
Patent number
US08216856B2

Reaction notes

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