Benzyl Bromide → HCID 86589054, compound

HRID 2414381Notes

Reaction equation

HRID 2414381 reaction equation
[OH:1][C@H:2]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[CH:8]=1)[C:3]([OH:5])=[O:4].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C>CCOC(C)=O>[OH:1][C@H:2]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[CH:8]=1)[C:3]([O:5][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:4]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 39237242HCID 39237242, compound

Product 1

HCID 86589054HCID 86589054, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of (R)-2-hydroxy-3-(3-methylphenyl)-propionic acid (6.3 g, 35.0 mmol), benzyl bromide (5.4 mL, 45.5 mmol) and triethylamine (7.31 mL, 52.4 mmol) in EtOAc (100 mL) is refluxed for 6 hours. After cooling, the solution is washed with 1 N HCl (150 mL), water (200 mL), sat'd NaHCO3 (200 mL) and brine (300 mL), dried (MgSO4), evaporated and chromatographed (silica, 10% EtOAc/hexane) to yield benzyl (R)-2-hydroxy-3-(3-methylphenyl)-propionate, as a clear oil.

Workup

  1. temperatureAfter cooling
  2. washthe solution is washed with 1 N HCl (150 mL), water (200 mL), sat'd NaHCO3 (200 mL) and brine (300 mL)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customchromatographed (silica, 10% EtOAc/hexane)

Sources & evidence

ORD record
ord-c2e552b274af4973ac5352dc789dda24
Source dataset
uspto-grants-2004_11
Patent number
US06812237B2

Reaction notes

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