2'-Methoxyacetophenone → (1R)-1-(2-methoxyphenyl)ethan-1-ol

HRID 1349447Notes

Reaction equation

HRID 1349447 reaction equation
B(Cl)([C@@H]1[C@@H](C)[C@H]2C(C)(C)[C@H](C2)C1)[C@@H]1[C@@H](C)[C@H]2C(C)(C)[C@H](C2)C1.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:31](=[O:33])[CH3:32]>O1CCCC1>[CH3:23][O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C@H:31]([OH:33])[CH3:32]

Participants

4

Reactant 2

HCID 684812'-MethoxyacetophenoneHCID 9923113Chlorobis((1S,2R,3S,5S)-2,6,6-trimethylbicyclo(3.1.1)hept-3-yl)borane

Product 1

HCID 643317(1R)-1-(2-methoxyphenyl)ethan-1-olYield 75.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-25 °C

Procedure

To a solution of (+)-B-chlorodiisopinocampheylborane (10.5 g) in tetrahydrofuran (50 ml) was added dropwise 2′methoxyacetophenone (10.5 g) at −25° C. The mixture was stirred at −25° C. for 1 hr and concentrated under reduced pressure. To the residue were added diethyl ether (100 ml) and diethanolamine (18.1 g) and the reaction mixture was stirred at room temperature for 2 hr. The precipitated solid was filtered off. The filtrate was concentrated under reduced pressure and purified by distillation under reduced pressure (bp 74–77° C./1 mmHg) to give the title compound (8.00 g).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionTo the residue were added diethyl ether (100 ml) and diethanolamine (18.1 g)
  3. stirringthe reaction mixture was stirred at room temperature for 2 hr
  4. filtrationThe precipitated solid was filtered off
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. distillationpurified by distillation under reduced pressure (bp 74–77° C./1 mmHg)

Sources & evidence

ORD record
ord-dd27a7b685d449708c8f368841ab3425
Source dataset
uspto-grants-2007_05
Patent number
US07211685B2

Reaction notes

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