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

HRID 2095348ノート

反応式

HRID 2095348 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1d1c1611ad024687886d4fa65b9a515b
出典データセット
uspto-grants-2013_05
特許番号
US08445684B2

反応ノート

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