Tetrahydrofuran → (R)-1-(3,4,5-Trifluorophenyl)ethanol

HRID 73435Notes

Reaction equation

HRID 73435 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:11])[C:9]=1[F:10])[CH:5]=[O:6].[CH2:12]1COCC1>>[F:1][C:2]1[CH:3]=[C:4]([CH:5]([OH:6])[CH3:12])[CH:7]=[C:8]([F:11])[C:9]=1[F:10]

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 27769543,4,5-Trifluorobenzaldehyde

Product 1

HCID 59386327(R)-1-(3,4,5-Trifluorophenyl)ethanol

Procedure

An ethereal solution (17.41 ml, 52.24 mmol, 3M) of MeMgEr was slowly added at −78° C. to a solution of 3,4,5-trifluorobenzaldehyde (6.96 g, 43.53 mmol) in THF (125 ml). The reaction mixture was stirred at room temperature for 16 h and was cooled (0° C.) and was quenched, sequentially, with excess ethyl acetate (10 ml) and water (5 ml). Excess anhydrous MgSO4 (5 g) was added and stirred for 30 minutes at room temperature. The suspension was filtered over celite and the solids were washed with ethyl acetate (2×25 ml). The combined filtrate was evaporated to obtain the product in quantitative yield (7.65 g).

Workup

  1. temperaturewas cooled (0° C.)
  2. customwas quenched
  3. additionExcess anhydrous MgSO4 (5 g) was added
  4. stirringstirred for 30 minutes at room temperature
  5. filtrationThe suspension was filtered over celite
  6. washthe solids were washed with ethyl acetate (2×25 ml)
  7. customThe combined filtrate was evaporated
  8. customto obtain the product in quantitative yield (7.65 g)

Sources & evidence

ORD record
ord-905d8ce294384308bd8dfc3a1e444e41
Source dataset
uspto-grants-2014_09
Patent number
US08829052B2

Reaction notes

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