反応式
B.[CH:2]([C:5]1[CH:6]=[CH:7][C:8]([O:24][CH3:25])=[C:9]([C:11]2[C:12]([C:21](O)=[O:22])=[CH:13][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:16]=2)[CH:10]=1)([CH3:4])[CH3:3].C(C1C=CC(OC)=C(C2C(C(N)=O)=CC(C(F)(F)F)=CC=2)C=1)(C)C>C1COCC1>[CH:2]([C:5]1[CH:6]=[CH:7][C:8]([O:24][CH3:25])=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:18])([F:19])[F:20])=[CH:13][C:12]=2[CH2:21][OH:22])[CH:10]=1)([CH3:4])[CH3:3]参加物
反応物 3
生成物 1
試薬・触媒・溶媒 1
実験手順
A solution of borane in THF (1 M, 859 μL, 0.859 mmol) was added dropwise to a stirred solution of 5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-carboxylic acid and 5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-carboxamide (3:1, 96.8 mg, 0.286 mmol) in dry THF at room temperature under N2. The reaction was stirred at room temperature for 3 h and carefully quenched with water (10 mL). The mixture was extracted with EtOAc (3×20 mL) and the combined extracts were washed with brine, dried (Na2SO4) and concentrated in vacuo to give the crude product. This was purified by flash chromatography (Si, 125×160 mm, 0-30% EtOAc in hexanes gradient) to afford [5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methanol as a colorless oil. Rf=0.27 (10% EtOAc/hexanes). 1H NMR (CDCl3, 500 MHz) δ 7.89 (br s, 1H), 7.62 (dd, J=8.0, 1.3 Hz, 1H), 7.36 (d, J=8.0 Hz, 1H), 7.29 (dd, J=8.5, 2.3 Hz, 1H), 7.03 (d, J=2.3 Hz, 1H), 6.96 (d, J=8.5, 1H), 4.51 (m, 2H), 3.74 (s, 3H), 2.93 (septet, J=7.0 Hz, 1H), 2.51 (s, 1H), 1.29 (d, J=7.0 Hz, 6H).
後処理
- customcarefully quenched with water (10 mL)
- extractionThe mixture was extracted with EtOAc (3×20 mL)
- washthe combined extracts were washed with brine
- dry with materialdried (Na2SO4)
- concentrationconcentrated in vacuo
- customto give the crude product
- customThis was purified by flash chromatography (Si, 125×160 mm, 0-30% EtOAc in hexanes gradient)
出典と根拠
- ORDレコード
- ord-e201db5433f14aa48d3192ab9897c227
- 出典データセット
- uspto-grants-2014_05
- 特許番号
- US08735435B2
関連ノート
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