Sodium Iodide → 7-methoxycarbonyl-2-oxohexahydro-3,5-methano-2H-cyclopenta[b]furan-6-yl 2-(methacryloyloxy)-acetate

HRID 252898Notes

Reaction equation

HRID 252898 reaction equation
Cl[CH2:2][C:3]([O:5][CH:6]1[CH:10]2[O:11][C:12](=[O:19])[CH:13]3[CH:14]([C:15]([O:17][CH3:18])=[O:16])[CH:7]1[CH2:8][CH:9]23)=[O:4].CN(C)C=O.[C:25]([O-:30])(=[O:29])[C:26]([CH3:28])=[CH2:27].[Na+].[I-].[Na+]>O>[C:25]([O:30][CH2:2][C:3]([O:5][CH:6]1[CH:10]2[O:11][C:12](=[O:19])[CH:13]3[CH:14]([C:15]([O:17][CH3:18])=[O:16])[CH:7]1[CH2:8][CH:9]23)=[O:4])(=[O:29])[C:26]([CH3:28])=[CH2:27]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6228Dimethylformamide2×HCID 3255932Sodium methacrylateHCID 578958527-methoxycarbonyl-2-oxohexahydro-3,5-methano-2H-cyclopenta[b]furan-6-yl 2-chloroacetate

Product 1

HCID 250672047-methoxycarbonyl-2-oxohexahydro-3,5-methano-2H-cyclopenta[b]furan-6-yl 2-(methacryloyloxy)-acetateYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 28.9 g of the 2-chloroacetic ester obtained in Example 1-1-1 and 40 g of dimethylformamide was added dropwise to a mixture of 12.4 g of sodium methacrylate, 3.0 g of sodium iodide and 50 g of dimethylformamide at a temperature below 30° C. The mixture was stirred at the temperature for 8 hours. 100 ml of water was added below 30° C. This was followed by ordinary post-treatment and recrystallization from toluene and n-hexane, obtaining 29.1 g of the target compound (yield 86%).

Workup

  1. customThis was followed by ordinary post-treatment and recrystallization from toluene and n-hexane

Sources & evidence

ORD record
ord-d4137679eabc48148aa860a03540b4de
Source dataset
uspto-grants-2011_01
Patent number
US07871752B2

Reaction notes

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