Sodium Iodide → 7-methoxycarbonyl-2-oxohexahydro-3,5-methano-2H-cyclopenta[b]furan-6-yl 4-(methacryloyloxy)butyrate

HRID 1172024Notes

Reaction equation

HRID 1172024 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([O:7][CH:8]1[CH:12]2[O:13][C:14](=[O:21])[CH:15]3[CH:16]([C:17]([O:19][CH3:20])=[O:18])[CH:9]1[CH2:10][CH:11]23)=[O:6].CN(C)C=O.[C:27]([O-:32])(=[O:31])[C:28]([CH3:30])=[CH2:29].[Na+].[I-].[Na+]>O>[C:27]([O:32][CH2:2][CH2:3][CH2:4][C:5]([O:7][CH:8]1[CH:12]2[O:13][C:14](=[O:21])[CH:15]3[CH:16]([C:17]([O:19][CH3:20])=[O:18])[CH:9]1[CH2:10][CH:11]23)=[O:6])(=[O:31])[C:28]([CH3:30])=[CH2:29]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6228Dimethylformamide2×HCID 3255932Sodium methacrylateHCID 578671007-methoxycarbonyl-2-oxohexahydro-3,5-methano-2H-cyclopenta[b]furan-6-yl 4-chlorobutyrate

Product 1

HCID 578670977-methoxycarbonyl-2-oxohexahydro-3,5-methano-2H-cyclopenta[b]furan-6-yl 4-(methacryloyloxy)butyrateYield 70.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 10.0 g of the 4-chlorobutyrate obtained in Example 1-1-1 and 30 g of dimethylformamide was added dropwise to a mixture of 4.69 g of sodium methacrylate, 0.71 g of sodium iodide and 20 g of dimethylformamide at 60-70° 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 work-up and silica gel chromatography purification, obtaining 8.12 g of the target compound (yield 70%).

Workup

  1. customThis was followed by ordinary work-up and silica gel chromatography purification

Sources & evidence

ORD record
ord-2036f849c372417ba80a46bd90f35c86
Source dataset
uspto-grants-2010_11
Patent number
US07833694B2

Reaction notes

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