Triethylamine → Tert-butyl 6-methacryloyl-2-oxohexahydro-3,5-methano-2h-cyclopenta[b]furan-7-carboxylate

HRID 558048Notes

Reaction equation

HRID 558048 reaction equation
O[CH:2]1[CH:6]2[O:7][C:8](=[O:18])[CH:9]3[CH:10]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:3]1[CH2:4][CH:5]23.C(N(CC)CC)C.[C:26](Cl)(=[O:30])[C:27]([CH3:29])=[CH2:28].C(=O)([O-])O.[Na+]>C(#N)C>[C:26]([CH:2]1[CH:6]2[O:7][C:8](=[O:18])[CH:9]3[CH:10]([C:11]([O:13][C:14]([CH3:16])([CH3:15])[CH3:17])=[O:12])[CH:3]1[CH2:4][CH:5]23)(=[O:30])[C:27]([CH3:29])=[CH2:28]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 13528Methacryloyl chloride2×HCID 516892Sodium BicarbonateHCID 57824120HCID 57824120, compound

Product 1

HCID 67000815Tert-butyl 6-methacryloyl-2-oxohexahydro-3,5-methano-2h-cyclopenta[b]furan-7-carboxylateYield 72.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In 2,500 ml of acetonitrile were dissolved 500 g of tert-butyl 6-hydroxy-2-oxohexahydro-3,5-methano-2H-cyclopenta[b]furan-7-carboxylate and 318 g of triethylamine. To the solution below 15° C., 288 g of methacrylic chloride was added dropwise. The solution was stirred at room temperature for 2 hours, another 32 g of methacrylic chloride added, and the solution stirred overnight. A saturated aqueous solution of sodium hydrogen carbonate, 500 ml, was added to the reaction solution, followed by ordinary work-up. Recrystallization from hexane yielded 437 g of the title compound (yield 69%).

Workup

  1. stirringthe solution stirred overnight
  2. customRecrystallization from hexane

Sources & evidence

ORD record
ord-64bb5ddb112048529b1bf2d67cf41ffa
Source dataset
uspto-grants-2011_11
Patent number
US08062831B2

Reaction notes

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