Tetrahydrofuran → 1-Cyclopropyl-1-(4-fluorophenyl)ethanol

HRID 1764884Notes

Reaction equation

HRID 1764884 reaction equation
C1(C2C=C(F)C=C[C:5]=2[C:11]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=2[CH:20]2[CH2:22][CH2:21]2)=O)CC1.C[Mg]Br.C1C[O:29]CC1>CCOCC>[CH:20]1([C:14]([C:13]2[CH:11]=[CH:5][C:16]([F:19])=[CH:17][CH:18]=2)([OH:29])[CH3:15])[CH2:21][CH2:22]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 53737258Cyclopropyl-4-fluorophenyl ketoneHCID 178418573HCID 178418573, compound

Product 1

HCID 981041-Cyclopropyl-1-(4-fluorophenyl)ethanolYield 89%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of cyclopropyl-4-fluorophenyl ketone (523 mg, 3.19 mmol) in THF (10 mL) at 0° C. under N2 was added 3 M methyl magnesium bromide (1.7 mL, 5.1 mmol) in Et2O. After 90 minutes at 0° C., the reaction was quenched by addition of brine (10 mL) and diluted with Et2O (100 mL). The organic solution was washed with saturated NaHCO3 (100 mL) and brine (100 mL). Column purification (hexanes:EtOAc 9:1) yielded 1-cyclopropyl-1-(4-fluorophenyl)ethanol (512 mg, 89%) as a colorless oil.

Workup

  1. customthe reaction was quenched by addition of brine (10 mL)
  2. additiondiluted with Et2O (100 mL)
  3. washThe organic solution was washed with saturated NaHCO3 (100 mL) and brine (100 mL)
  4. customColumn purification (hexanes:EtOAc 9:1)

Sources & evidence

ORD record
ord-b05d5de93ae146ae84332d77b61aadb1
Source dataset
uspto-grants-2007_06
Patent number
USRE039679E1

Reaction notes

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