Triethyl phosphonoacetate → Methyl Benzofuran-3-acetate

HRID 1095542Notes

Reaction equation

HRID 1095542 reaction equation
CC([O-])(C)C.[K+].C[CH2:8][O:9][C:10]([CH2:12]P(OCC)(OCC)=O)=[O:11].[O:21]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[C:23](=O)[CH2:22]1>CN(C=O)C.O=O>[CH3:8][O:9][C:10](=[O:11])[CH2:12][C:23]1[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[O:21][CH:22]=1

Participants

6

Reactant 3

HCID 13345Triethyl phosphonoacetateHCID 23556CoumaranoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 10976279Methyl Benzofuran-3-acetate

Reagents, catalysts & solvents 2

HCID 977OxygenSolventHCID 6228DimethylformamideSolvent2×

Procedure

KOtBu (0.673 g, 6 mmol) was dissolved in dry DMF (10 ml) with exclusion of oxygen. Phosphonoacetic acid triethyl ester (0.87 ml, 6 mmol) was then added to the mixture. After 20 min a solution of benzofuran-3(2H)-one (0.536 g, 4 mmol) in dry DMF (10 ml, argon atmosphere) was added to this mixture. The reaction mixture was stirred at room temperature for 1 h and thereafter poured on to ice (50 ml) for working up. The mixture obtained was extracted with diethyl ether (4×20 ml). The organic phase was washed with water (4×20 ml), dried with Na2SO4 and then concentrated. The product formed was purified by column chromatography [silica gel 60 (50 g); cyclohexane, ethyl acetate (4:1)] and obtained in a yield of 0.372 g (48%) as a yellowish oil.

Workup

  1. customThe mixture obtained
  2. extractionwas extracted with diethyl ether (4×20 ml)
  3. washThe organic phase was washed with water (4×20 ml)
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated
  6. customThe product formed
  7. customwas purified by column chromatography [silica gel 60 (50 g); cyclohexane, ethyl acetate (4:1)]
  8. customobtained in a yield of 0.372 g (48%) as a yellowish oil

Sources & evidence

ORD record
ord-59d2d9c549a0457c91d3ff58936a4e86
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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