2-Benzylacrylic Acid → HCID 14158055, compound

HRID 345013Notes

Reaction equation

HRID 345013 reaction equation
C[Si](C([Si](C)(C)C)C(N)=O)(C)C.[CH2:13]([C:20](=[CH2:24])[C:21]([OH:23])=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[P:25]([O-:32])([O:29][CH2:30][CH3:31])[O:26][CH2:27][CH3:28]>ClCCl.C(OCC)(=O)C>[CH2:27]([O:26][P:25]([CH2:24][CH:20]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:21]([OH:23])=[O:22])([O:29][CH2:30][CH3:31])=[O:32])[CH3:28]

Participants

6

Reactant 3

HCID 3035712-Benzylacrylic AcidHCID 3780918DiethylphosphiteHCID 11708267Bistrimethylsilylacetamid

Product 1

HCID 14158055HCID 14158055, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Bis(trimethylsilyl)acetamide (5 g, 0.024 mole, 6 ml) was added, at room temperature, to a solution of benzyl acrylic acid (2 g, 0.012 mole) and diethyl phosphite (3.3 g, 0.024 moles) in dichloromethane (30 ml). The mixture was stirred at ambient temperature for 30 minutes, concentrated in vacuo at room temperature, and the residue was heated at a bath temperature of 100°-110° for 16 hours. The colorless oil reaction mixture was dissolved in ethyl acetate and extracted with 5% sodium bicarbonate (pH 9-10). The aqueous alkaline solution was washed with ether and acidified to a pH of 1-2 with concentrated hydrochloric acid. The colorless oil that separated was extracted into ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to give a colorless oil (3.6 g).

Workup

  1. concentrationconcentrated in vacuo at room temperature
  2. temperaturethe residue was heated at a bath temperature of 100°-110° for 16 hours
  3. customThe colorless oil reaction mixture
  4. extractionextracted with 5% sodium bicarbonate (pH 9-10)
  5. washThe aqueous alkaline solution was washed with ether
  6. customThe colorless oil that separated
  7. extractionwas extracted into ethyl acetate
  8. washwashed with brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7e4bb5333ad7446cb24a44b543d09425
Source dataset
uspto-grants-1991_10
Patent number
US05055466

Reaction notes

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