Chloride → HCID 86688830, compound
Reaction equation
[H-].[Na+].[C:3]([O:19][CH2:20][CH3:21])(=[O:18])[CH2:4][C:5]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])([C:7]([O:9][CH2:10][CH3:11])=[O:8])[OH:6].[Cl-]>C1COCC1>[C:7]([OH:9])(=[O:8])[CH2:5][CH2:4][CH3:3].[C:13]([O:15][CH2:16][CH3:17])(=[O:14])[CH2:12][C:5]([CH2:4][C:3]([O:19][CH2:20][CH3:21])=[O:18])([C:7]([O:9][CH2:10][CH3:11])=[O:8])[OH:6]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of sodium hydride (0.651 g, 1.5 eq) in THF at 0° C., triethyl citrate (5 g, 1 eq) in THF (50 ml) was added drop wise and stirred for 1 h at 0° C. Then butaryl chloride (2.12 g, 1.1 eq) was added drop wise and stirred for 1 h at 0° C. under nitrogen atmosphere. The stirring was continued for another 12 h at 25-30° C. The reaction was monitored by thin layer chromatography. The reaction was quenched with cold water and extracted with ethyl acetate. Ethyl acetate layer was washed with sodium bicarbonate solution (10%) followed by water and brine solution. The organic layer was dried over sodium sulphate and concentrated to get the crude product. The crude product was purified by column chromatography using 6% ethyl acetate in petroleum ether as eluent. The product was characterized by NMR. Yield was 3 g; 48.6%.
Workup
- stirringstirred for 1 h at 0° C. under nitrogen atmosphere
- waitThe stirring was continued for another 12 h at 25-30° C
- customThe reaction was quenched with cold water
- extractionextracted with ethyl acetate
- washEthyl acetate layer was washed with sodium bicarbonate solution (10%)
- dry with materialThe organic layer was dried over sodium sulphate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-287580a444154d1eb86e2d5d194a4173
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09127232B2
Reaction notes
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