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

HRID 2073604Notes

Reaction equation

HRID 2073604 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 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 washings and filtrate were concentrated. Distillation furnished [S]-(-)-1-chloro-3-phenyl-3-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 washings and filtrate were concentrated
  6. distillationDistillation

Sources & evidence

ORD record
ord-ab0f86dd6b4f415e9eada51edc0c8541
Source dataset
uspto-grants-1990_04
Patent number
US04918207

Reaction notes

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