Ethyl bromoacetate → HCID 66747913, compound

HRID 1464961Notes

Reaction equation

HRID 1464961 reaction equation
[H-].[Na+].[O:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]([OH:13])[CH2:5][CH2:4]1.Br[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]>C1COCC1>[O:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]([O:13][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 92890Chroman-4-ol

Product 1

HCID 66747913HCID 66747913, compoundYield 51.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of sodium hydride (60% in mineral oil, 173 mg, 4.33 mmol) in THF was added chroman-4-ol (500 mg, 3.33 mmol) at 0° C. After being stirred at the same temperature for 15 min, ethyl bromoacetate (723 mg, 4.33 mmol) was added. After 1 h, the mixture was poured onto water, and the aqueous phase was extracted with EtOAc (twice). The combined organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with hexane/EtOAc (7:1-4:1) to give 404 mg (51% yield) of the title compound as a colorless oil.

Workup

  1. waitAfter 1 h
  2. additionthe mixture was poured onto water
  3. extractionthe aqueous phase was extracted with EtOAc (twice)
  4. dry with materialThe combined organic layer was dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel eluting with hexane/EtOAc (7:1-4:1)

Sources & evidence

ORD record
ord-e578a3be741447fd83b9e5e20b9d7b5f
Source dataset
uspto-grants-2015_04
Patent number
US08999974B2

Reaction notes

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