Epibromohydrin → 2-(Oxiran-2-ylmethoxy)indane

HRID 1280417Notes

Reaction equation

HRID 1280417 reaction equation
[H-].[Na+].[CH2:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH:4]1[OH:12].[CH2:13]([CH:15]1[O:17][CH2:16]1)Br>CN(C=O)C>[O:17]1[CH2:16][CH:15]1[CH2:13][O:12][CH:4]1[CH2:5][C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:3]1

Participants

5

Reactant 3

HCID 18430EpibromohydrinHCID 24758Sodium hydrideHCID 779362-Indanol

Product 1

HCID 155803392-(Oxiran-2-ylmethoxy)indane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a solution of 60% NaH (0.18 g, 4.5 mmol) in DMF (10 ml) cooled to 0 degrees was added 2-indanol (0.5 g, 3,73 mmol) in DMF (2 ml) dropwise. After stirring for 30 minutes epibromohydrin (1.11 g, 8.18 mmol) in DMF (1 ml) was added dropwise. The reaction was allowed to warm to room temperature and stirred for 48 h. The solvent was removed in vacuo and the residue was purified using Prep TLC (30:1, DCM:MeOH) to afford compound 6.

Workup

  1. additionwas added dropwise
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified

Sources & evidence

ORD record
ord-1039b6bb9d74427cbdcce34a71886dec
Source dataset
uspto-grants-2002_09
Patent number
US06451798B2

Reaction notes

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