Boron trifluoride etherate → HCID 86718005, compound

HRID 1500467Notes

Reaction equation

HRID 1500467 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:10]=1Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li]CCCC.[CH3:22][C@H:23]1[CH2:25][O:24]1.B(F)(F)F.CCOCC>C1COCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:10]=1[CH2:22][C@@H:23]([OH:24])[CH3:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 146262(2S)-2-MethyloxiraneHCID 107312131-(benzyloxy)-2-bromo-4-methylbenzeneHCID 178418339Butyllithium

Product 1

HCID 86718005HCID 86718005, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(benzyloxy)-2-bromo-4-methylbenzene (3a) (1.0 g, 3.6 mmol) in THF (20 mL) at −78° C. under N2 atmosphere was added n-BuLi (2.5 M, 1.6 mL, 3.9 mmol), the resulting mixture was stirred for 30 min and (S)-2-methyloxirane (0.38 mL, 5.4 mmol) and BF3.Et2O (0.67 mL, 5.4 mmol) were added to the mixture. It was stirred at −78° C. for 1.5 h and warmed up to ambient temperature, quenched with water (10 mL), extracted with EtOAc (30 mL), washed with brine, dried and concentrated. The residue was purified by column chromatography on silica gel eluting with hexanes/EtOAc (10:1) to give the title compound (3b).

Workup

  1. stirringIt was stirred at −78° C. for 1.5 h
  2. customquenched with water (10 mL)
  3. extractionextracted with EtOAc (30 mL)
  4. washwashed with brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel eluting with hexanes/EtOAc (10:1)

Sources & evidence

ORD record
ord-c96228abe207436d9a79197915c9f290
Source dataset
uspto-grants-2015_12
Patent number
US09206166B2

Reaction notes

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