Acetonitrile → HCID 57562221, compound

HRID 75082Notes

Reaction equation

HRID 75082 reaction equation
C(#N)C.[OH:4][CH:5]1[CH:9]2[O:10][C:11](=[O:21])[CH:12]3[CH:13]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:6]1[CH2:7][CH:8]23.C(N(CC)CC)C.[C:29](Cl)(=[O:33])[C:30]([CH3:32])=[CH2:31]>O>[C:29]([O:4][CH:5]1[CH:9]2[O:10][C:11](=[O:21])[CH:12]3[CH:13]([C:14]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:15])[CH:6]1[CH2:7][CH:8]23)(=[O:33])[C:30]([CH3:32])=[CH2:31]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 57824120HCID 57824120, compound

Product 1

HCID 57562221HCID 57562221, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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%).

Workup

  1. customat 20° C.
  2. customRecrystallization

Sources & evidence

ORD record
ord-11d568bbeb384deb8068151b90e61451
Source dataset
uspto-grants-2014_09
Patent number
US08835097B2

Reaction notes

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