Benzyl Bromide → HCID 131721355, compound

HRID 617118Notes

Reaction equation

HRID 617118 reaction equation
[CH2:1]1[O:3][C@@H:2]1[CH2:4][OH:5].[CH:6]1[CH:11]=[CH:10][C:9]([CH2:12]Br)=[CH:8][CH:7]=1.[H-].[Na+]>CN(C=O)C>[CH2:1]1[O:3][C@@H:2]1[CH2:4][OH:5].[CH2:12]([O:5][CH2:4][C:2]1[CH:8]=[CH:7][CH:6]=[CH:11][CH:1]=1)[C:9]1[CH:10]=[CH:11][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 5460455(+)-Glycidol

Product 1

HCID 131721355HCID 131721355, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of (R)-glycidol (25 g, 0.337 mol) and BnBr (60.2 mL, 0.506 mol) in anhydrous DMF (1 L) was slowly added NaH (16.2 g of 60% oil dispersion, 0.405 mol) at 0° C. The mixture was warmed to room temperature and stirred for 3 hours. The mixture was concentrated in vacuo. After aqueous work-up (CH2Cl2) and chromatography, 44.8 g of the benzyl ether was obtained: [α]25D -1.6° (c 0.63, CHCl3). 1H NMR (CDCl3): δ2.60 (1H, dd, J=2.5, 5.0), 2.79 (1H, dd, J=4.4, 5.0), 3.17 (1H, m), 3.43 (1H, dd, J=5.7, 11.5), 3.75 (1H, dd, J=3.0, 11.5), 4.57 (2H, AB q, J=11.9), 7.32-7.34 (5H, m). 13C NMR (CDCl3): δ44.3, 50.8, 70.8, 73.3, 127.7, 128.4, 137.8. HRMS (EI) calcd for C10H12O2 164.0837, found 164.0803.

Workup

  1. customat 0° C
  2. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-f0f0330aa7f1434fa80c0d983f2f8616
Source dataset
uspto-grants-1999_09
Patent number
US05948770

Reaction notes

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