Sodium hydride → Methyl 2-[(4-bromobenzyl)oxy]-4-methylpentanoate

HRID 1744066Notes

Reaction equation

HRID 1744066 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH:13]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:14]([O:16][CH3:17])=[O:15]>CN(C=O)C.C(OCC)C.C(OCC)(=O)C.O.C(=O)(O)[O-]>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][O:7][CH:13]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:14]([O:16][CH3:17])=[O:15])=[CH:4][CH:3]=1

Participants

9

Reactant 3

HCID 24758Sodium hydrideHCID 701194-Bromobenzyl alcoholHCID 12957039Methyl 2-bromo-4-methylpentanoate

Product 1

HCID 22235862Methyl 2-[(4-bromobenzyl)oxy]-4-methylpentanoate

Reagents, catalysts & solvents 5

HCID 769Bicarbonate IonSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Bromobenzylalcohol (1.1 g, 5.9 mmoles) in 12 mL of DMF was treated with sodium hydride (260 mg, 60% oil dispersion, 6.5 mmoles) and stirred for 30 minutes. Methyl 2-bromo-4-methylpentanoate (1.1 mL, 6.8 mmoles) was added in one portion and the reaction was stirred overnight. The reaction was diluted with diethyl ether, ethyl acetate, water and sat. aq. bicarbonate. The phases were separated and the organic phase was washed with 2 portions of 1.2 N hydrochloric acid and then brine. The organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure to yield a residue which was purified by flash chromatography to afford methyl 2-[(4-bromobenzyl)oxy]-4-methylpentanoate.

Workup

  1. stirringthe reaction was stirred overnight
  2. customThe phases were separated
  3. washthe organic phase was washed with 2 portions of 1.2 N hydrochloric acid
  4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto yield a residue which
  7. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-3da6bc64ee7c4a90afb4e0661ce48cb2
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

Loading…