Benzyl Bromide → HCID 54241024, compound

HRID 2301173Notes

Reaction equation

HRID 2301173 reaction equation
[CH3:1][C:2]([CH3:9])([CH3:8])[C@H:3]([OH:7])[C:4]([OH:6])=[O:5].C(N(CC)CC)C.[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(OCC)(=O)C>CN(C=O)C>[CH2:17]([O:5][C:4](=[O:6])[C@@H:3]([OH:7])[C:2]([CH3:9])([CH3:8])[CH3:1])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 11097105(2S)-2-hydroxy-3,3-dimethylbutanoic acid

Product 1

HCID 54241024HCID 54241024, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S)-3,3-dimethyl-2-hydroxybutyric acid (2.1 grams, 15.9 mmol) and triethylamine (3.3 mL, 23.8 mmoL) were dissolved in 15 mL DMF. Benzylbromide (2.8 mL, 23.8 mmol) was added and the mixture was stirred overnight. Ethyl acetate was added and the mixture was washed with water (3×) and sat'd NaCl then dried over sodium sulfate and concentrated. Flash chromatography (150 g silica, 7/1Hexane/EtOAc) afforded 3.4 grams (96%) of the title compound. 1H NMR (300 MHz, CDCl3). δ 0.98 (s, 9H), 2.75 (d, 1H), 3.85 (d, 1H), 5.23, (s, 2H), 7.27-7.3 (m, 5H).

Workup

  1. washthe mixture was washed with water (3×)
  2. dry with materialthen dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-630956b1a35e43689032f019d062b435
Source dataset
uspto-grants-2002_12
Patent number
US06498161B1

Reaction notes

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