Boron trifluoride etherate → HCID 86718005、化合物

HRID 1500467ノート

反応式

HRID 1500467 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 86718005HCID 86718005、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-c96228abe207436d9a79197915c9f290
出典データセット
uspto-grants-2015_12
特許番号
US09206166B2

反応ノート

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