3-Phenyllactic acid, (S)- → (2S)-3-Phenylpropane-1,2-diol

HRID 2095344Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2095344
[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

Komponenten

4

Edukt 2

HCID 4447183-Phenyllactic acid, (S)-HCID 2723981Borane;tetrahydrofuran

Produkt 1

HCID 446127(2S)-3-Phenylpropane-1,2-diolAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (S)-2-hydroxy-3-phenylpropanoic acid (4.98 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 (S)-3-phenylpropane-1,2-diol (4.13 g, 91%) as a colorless oil. LC-MS (ESI) m/z 153 (M+H+).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-39dede94eed0449f96974ee8bdce7014
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08445684B2

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