Tetrahydrofuran → (R)-1-(3-Chlorophenyl)-1,2-ethanediol

HRID 479005Notes

Reaction equation

HRID 479005 reaction equation
C1COCC1.[Cl:6][C:7]1[CH:8]=[C:9]([CH:15]=[CH:16][CH:17]=1)[C@@H:10]([OH:14])[C:11](O)=[O:12].[H]1[BH2][H][BH2]1.C1COCC1>CO>[Cl:6][C:7]1[CH:8]=[C:9]([C@@H:10]([OH:14])[CH2:11][OH:12])[CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 2733127(R)-2-(3-Chlorophenyl)-2-hydroxyacetic acid

Product 1

HCID 9815352(R)-1-(3-Chlorophenyl)-1,2-ethanediol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into THF (70 ml) were added (R)-3-chloromandelic acid (10 g) and further, under ice-cooling and dropwise, a 1M-diborane THF solution (81.5 ml) over 2 hours, and then stirring was continued at 25° C. for 12 hours. The reaction mixture was cooled, methanol (20 ml) was added thereto over 30 minutes and then stirring was further continued for 3 hours. The resulting reaction mixture was concentrated and then the residue was recrystallized from diethyl ether to obtain a colorless oily compound mentioned above (7.3 g, 78.9%).

Workup

  1. temperaturefurther, under ice-cooling
  2. temperatureThe reaction mixture was cooled
  3. waitover 30 minutes
  4. stirringstirring
  5. waitwas further continued for 3 hours
  6. customThe resulting reaction mixture
  7. concentrationwas concentrated
  8. customthe residue was recrystallized from diethyl ether
  9. customto obtain a colorless oily compound

Sources & evidence

ORD record
ord-a4cb89a579f648c493e0be9948310faf
Source dataset
uspto-grants-2003_11
Patent number
US06642395B1

Reaction notes

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