反応式
[CH3:1][C:2]1([CH3:26])[CH2:11][CH2:10][C:9](=O)[C:8]2[CH:7]=[C:6](/[CH:13]=[CH:14]/[C:15]3[CH:25]=[CH:24][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][CH:16]=3)[CH:5]=[CH:4][C:3]1=2.[CH2:27]([SH:31])[CH2:28][CH2:29][SH:30].[CH2:32](Cl)Cl>C(=O)([O-])[O-].[K+].[K+]>[CH3:1][C:2]1([CH3:26])[CH2:11][CH2:10][CH:9]([CH:32]2[S:31][CH2:27][CH2:28][CH2:29][S:30]2)[C:8]2[CH:7]=[C:6](/[CH:13]=[CH:14]/[C:15]3[CH:25]=[CH:24][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][CH:16]=3)[CH:5]=[CH:4][C:3]1=2参加物
反応物 3
生成物 1
試薬・触媒・溶媒 1
実験手順
To a cold solution (0° C.) of 140 mg (0.40 mmol) of ethyl (E)-4-[2-(5,5-dimethyl-5,6,-dihydro-naphthalen-8(7H)-one-2-yl)ethenyl]-benzoate (Compound A2), in 6.0 mL of methylene chloride was added dropwise 130 mg (0.12 mL, 1.2 mmol) of 1,3-propanedithiol and 0.17 g (0.15 mL, 102 mmol) of borontrifluoride diethyl etherate. The reaction stirred between 0° C. and room temperature for 4 h. The mixture was diluted with aqueous sat. potassium carbonate, and extracted with ether (2×). The organic phase was washed with brine, dried over MgSO4 and then concentrated in vacuo. The crude product was purified by flash chromatography (silica, 10% ethyl acetate in hexane) to afford the title compound as a solid. 1H NMR (CDCl3): δ 1.29 (s, 6H), 1.39 (t, J=7.1 Hz, 3H), 1.83 (m, 2H), 2.00 (m, 1H), 2.09 (m, 1H), 2.62 (m, 2H), 2.74 (m, 2H), 3.17 (m, 2H), 4.36 (q, J=7.1 Hz, 2H), 7.09 (d, J=16.4 Hz, 1H), 7.20 (d, J=16.4 Hz, 1H), 7.30 (d, J=8.2 Hz, 1H), 7.41 (dd, J=1.9, 8.2 Hz, 1H), 7.55 (d, J=8.4 Hz, 2H), 8.00 (d, J=8.4 Hz, 1H), 8.10 (d, J=1.9 Hz, 2H).
後処理
- extractionextracted with ether (2×)
- washThe organic phase was washed with brine
- dry with materialdried over MgSO4
- concentrationconcentrated in vacuo
- customThe crude product was purified by flash chromatography (silica, 10% ethyl acetate in hexane)
出典と根拠
- ORDレコード
- ord-61b7b949db554319af6ea0bc4d4f4f1e
- 出典データセット
- uspto-grants-2003_11
- 特許番号
- US06653483B1
関連ノート
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