Boron trifluoride etherate → 2-(1-Chloro-3-methylnaphthalen-2-yl)-2-(1,1,1-trifluoro-2-methylpropan-2-yloxy)ethanol

HRID 926216ノート

反応式

HRID 926216 の反応式
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([CH3:12])[C:3]=1[C@@H:13]1[CH2:15][O:14]1.[F:16][C:17]([F:23])([F:22])[C:18]([OH:21])([CH3:20])[CH3:19].B(F)(F)F.CCOCC>C(Cl)Cl>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([CH3:12])[C:3]=1[CH:13]([O:21][C:18]([CH3:20])([CH3:19])[C:17]([F:23])([F:22])[F:16])[CH2:15][OH:14]

参加物

5

反応物 3

HCID 8000Boron trifluoride etherateHCID 681821,1,1-Trifluoro-2-methylpropan-2-olHCID 89676658(R)-2-(1-chloro-3-methylnaphthalen-2-yl)oxirane

生成物 1

HCID 896766802-(1-Chloro-3-methylnaphthalen-2-yl)-2-(1,1,1-trifluoro-2-methylpropan-2-yloxy)ethanol

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of (R)-2-(1-chloro-3-methylnaphthalen-2-yl)oxirane (340 mg, 1.56 mmol) and 2-trifluoromethyl-2-propanol (4.3 mL, 38.97 mmol) in CH2Cl2 (4.3 mL), boron trifluoride diethyl etherate (1.9 mL, 15.60 mmol) was added at 0° C. The reaction mixture was stirred for 16 h at 0° C. and allowed to warm to room temperature overnight. The mixture was quenched with saturated aqueous NaHCO3, and then diluted with CH2Cl2. The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated and purified by flash column chromatography (silica gel, 0 to 20% ethyl acetate/hexanes) to give 2-(1-chloro-3-methylnaphthalen-2-yl)-2-(1,1,1-trifluoro-2-methylpropan-2-yloxy)ethanol. 1H-NMR: 400 MHz, (CDCl3) δ 8.27 (d, J=8.4 Hz, 1H), 7.73 (d, J=7.6 Hz, 1H), 7.57-7.49 (m, 3H), 5.90 (dd, J=9.6, 4.4 Hz, 1H), 3.98 (t, J=11.2 Hz, 1H), 3.66 (dd, J=12.0, 4.0 Hz, 1H), 2.69 (s, 3H), 2.18 (br s, 1H), 1.45 (s, 3H), 1.19 (s, 3H).

後処理

  1. temperatureto warm to room temperature overnight
  2. customThe mixture was quenched with saturated aqueous NaHCO3
  3. additiondiluted with CH2Cl2
  4. washThe organic phase was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by flash column chromatography (silica gel, 0 to 20% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-9a6a2e6749bd4e8e80e6786dc0e216cb
出典データセット
uspto-grants-2016_03
特許番号
US09284323B2

反応ノート

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