Ethyl bromoacetate → HCID 14988926, compound

HRID 964365Notes

Reaction equation

HRID 964365 reaction equation
[OH:1][CH2:2][CH2:3][CH:4]1[O:6][C:5]1([CH:8]1[CH:15]([O:16][CH3:17])[CH:14]([O:18][C:19]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[O:20])[CH2:13][CH2:12][C:9]21[O:11][CH2:10]2)[CH3:7].[H-].[Na+].Br[CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32]>C1(C)C=CC=CC=1.CN(C)C=O>[CH2:34]([O:33][C:31]([CH2:30][O:1][CH2:2][CH2:3][CH:4]1[O:6][C:5]1([CH:8]1[CH:15]([O:16][CH3:17])[CH:14]([O:18][C:19]([N:21]2[CH2:22][CH2:23][O:24][CH2:25][CH2:26]2)=[O:20])[CH2:13][CH2:12][C:9]21[O:11][CH2:10]2)[CH3:7])=[O:32])[CH3:35]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 14988919HCID 14988919, compound

Product 1

HCID 14988926HCID 14988926, compoundYield 71.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-[3-(2-hydroxyethyl)-2-methyloxiranyl]-5-methoxy-6-(morpholinocarbonyloxy)-1-oxaspiro[2,5]octane (76.2 mg) in a mixture of toluene (2 ml) and N,N-dimethylformamide (1 ml) was added sodium hydride (20.5 mg) in one portion under ice cooling. The mixture was stirred for half an hour at the same temperature and ethyl bromoacetate (68.5 mg) was added. After stirred for 3 hours at ambient temperature, the reaction mixture was quenched with aqueous saturated ammonium chloride solution (2 ml). The organic layer was washed with brine, dried, and evaporated in vacuo. The residue was purified by column chromatography on silica gel (diethyl ether) to give 4-[3-(2-ethoxycarbonylmethoxyethyl)-2-methyl-oxiranyl]-5-methoxy-6-(morpholinocarbonyloxy)-1-oxaspiro-[2,5]octane (66.9 mg).

Workup

  1. additionwas added
  2. customthe reaction mixture was quenched with aqueous saturated ammonium chloride solution (2 ml)
  3. washThe organic layer was washed with brine
  4. customdried
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel (diethyl ether)

Sources & evidence

ORD record
ord-7d868978d97544eea8c1c812c4c3d8b8
Source dataset
uspto-grants-1998_06
Patent number
US05767293

Reaction notes

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