Reacción #162264

ord-11d568bbeb384deb8068151b90e61451

Ecuación de reacción

C=C(C)C(=O)Cl
methacryloyl chloride
CC#N
acetonitrile
CC(C)(C)OC(=O)C1C2CC3C(OC(=O)C31)C2O
tert-butyl 6-hydroxy-2-oxohexahydro-3,5-methano-2H-cyclopenta[b]furane-7-carboxylate
CCN(CC)CC
triethylamine
C=C(C)C(=O)OC1C2CC3C1OC(=O)C3C2C(=O)OC(C)(C)C
intended product
Rendimiento 70.3%
C=C(C)C(=O)OC1C2CC3C1OC(=O)C3C2C(=O)OC(C)(C)C
7-Tert-butoxycarbonyl-2-oxohexahydro-3,5-methano-2H-cyclopenta[b]furane-6-yl Methacrylate
Rendimiento 70.3%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otroat 20° C.
  2. 2
    OtroRecrystallization

Procedimiento

Dissolved into 900 mL of acetonitrile were 226.8 g of tert-butyl 6-hydroxy-2-oxohexahydro-3,5-methano-2H-cyclopenta[b]furane-7-carboxylate (24) and 135.2 g of triethylamine. Into this mixture was gradually added 121.1 g of methacryloyl chloride at 20° C. or lower. After the resulting mixture was stirred at room temperature for 3 hours, 300 g of water was added into it and usual work-up was carried out. Recrystallization was made from ethyl acetate to give 202.2 g of the intended product (Yield 70%).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08835097B2uspto-grants-2014_09