Boron trifluoride etherate → HCID 86718005, 화합물

HRID 1500467노트

반응식

HRID 1500467 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 86718005HCID 86718005, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-c96228abe207436d9a79197915c9f290
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206166B2

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