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

HRID 2095348노트

반응식

HRID 2095348 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-1d1c1611ad024687886d4fa65b9a515b
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08445684B2

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