(R)-3-phenyllactic acid → (R)-3-phenylpropane-1,2-diol

HRID 2095348Notes

Reaction equation

HRID 2095348 reaction equation
[OH:1][C@H:2]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3](O)=[O:4].B.C1COCC1>C1COCC1>[C:7]1([CH2:6][C@@H:2]([OH:1])[CH2:3][OH:4])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 643327(R)-3-phenyllactic acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 10953709(R)-3-phenylpropane-1,2-diolYield 94.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-2-hydroxy-3-phenylpropanoic acid (5.0 g, 30.0 mmol) in 100 mL of anhydrous THF was added slowly BH3.THF complex (90 mL, 1M in THF, 3.0 equiv.) with ice cooling under N2. The solution was stirred overnight at room temperature, and the reaction was quenched with water (Caution, copious H2 evolution). After evaporation of the solvent, the residue was diluted with water and extracted with EtOAc (3×50 mL). The combined organic layers were dried over Na2SO4 and concentrated to afford (R)-3-phenylpropane-1,2-diol (4.3 g, 94%) as a colorless oil. LC-MS (ESI) m/z 153 (M+H+). 1H NMR (CDCl3, 300 MHz) δ 7.37-7.23 (m, 5H), 4.02-3.94 (m, 1H), 3.74 (dd, 1H, J=11.1, 3.3 Hz), 3.54 (dd, 1H, J=11.1, 6.9 Hz), 2.85-2.74 (m, 2H).

Workup

  1. customthe reaction was quenched with water (Caution, copious H2 evolution)
  2. customAfter evaporation of the solvent
  3. additionthe residue was diluted with water
  4. extractionextracted with EtOAc (3×50 mL)
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1d1c1611ad024687886d4fa65b9a515b
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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