Diethanolamine → (S)-(-)-3-Chloro-1-phenyl-1-propanol

HRID 974652Notes

Reaction equation

HRID 974652 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].N(CCO)CCO>C1COCC1>[Cl:1][CH2:2][CH2:3][C@@H:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5]

Participants

4

Reactant 2

HCID 8113DiethanolamineHCID 702953-Chloropropiophenone

Product 1

HCID 2777894(S)-(-)-3-Chloro-1-phenyl-1-propanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-chloropropiophenone (8.93 g, 50 mmol in 25 ml THF) was added to (-) diisopinocampheylchloroborane (Ipc2BCl, 18.0 g, 56 mmole, in 25 ml THF at -24° C.). The reaction was complete within 7 hours after which all volatiles were removed under reduced pressure. The residue was dissolved in ether, and diethanolamine (2 equivalents) was added. The resulting suspension was stirred for two hours and filtered. The solid residue was washed with ether and the combined wasings and filtrate were concentrated. Distillation furnished [S]-(-)-3-chloro-1-phenyl-1-propanol. Yield: 6.1 g, 72%; mp 56°-57° C.; [α]D23 25.25, c=7.05, CHCl3 ; 97% ee.

Workup

  1. customafter which all volatiles were removed under reduced pressure
  2. dissolutionThe residue was dissolved in ether
  3. filtrationfiltered
  4. washThe solid residue was washed with ether
  5. concentrationthe combined wasings and filtrate were concentrated
  6. distillationDistillation

Sources & evidence

ORD record
ord-0039b83ec2334ed1ae71df48bf80e703
Source dataset
uspto-grants-1991_11
Patent number
US05068432

Reaction notes

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