反応式
I[C:2]1[CH:7]=[C:6]([O:8][CH:9]([CH3:11])[CH3:10])[CH:5]=[C:4]([O:12][CH:13]([CH3:15])[CH3:14])[CH:3]=1.[OH:16][CH2:17][C@@H:18]1[C@:27]2([CH3:28])[C@H:22]([C:23]([CH3:30])([CH3:29])[CH2:24][CH2:25][CH2:26]2)[CH2:21][CH2:20][C@@:19]1([CH3:32])[OH:31].C([O-])([O-])=O.[Cs+].[Cs+].COCCOCCOC>CCOC(C)=O.[Cu]I.C1(C)C=CC=CC=1>[CH3:14][CH:13]([O:12][C:4]1[CH:3]=[C:2]([CH:7]=[C:6]([O:8][CH:9]([CH3:11])[CH3:10])[CH:5]=1)[O:16][CH2:17][C@@H:18]1[C@:27]2([CH3:28])[C@H:22]([C:23]([CH3:30])([CH3:29])[CH2:24][CH2:25][CH2:26]2)[CH2:21][CH2:20][C@@:19]1([CH3:32])[OH:31])[CH3:15]参加物
反応物 4
生成物 1
試薬・触媒・溶媒 3
反応条件
- 温度
- 120 °C
実験手順
In a sealed tube purged with nitrogen, compound (47) (1.85 g, 5.78 mmol), (1S,2R,4aS,8aS)-1-(hydroxymethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol (3) (1.26 g, 5.25 mmol), Cs2CO3 (2.56 g, 7.87 mmol), 3,4,7,8-tetramethyl-[1,10]-phenylthroline (0.25 g, 1.0 mmol), CuI (0.10 g, 0.70 mmol), diglyme (5 mL) and toluene (20 mL) were placed. The reaction mixture was stirred at 120° C. for 18 h. The reaction was cooled to room temperature, diluted with EtOAc (600 mL) and washed with water (200 mL). The solid material was removed by filtration. The organic layer was separated, dried (Na2SO4) and concentrated. Purification by column chromatography on silica gel (Hexanes/EtOAc, 4:1) gave (1S,2R,4aS,8aS)-1-[3,5-bis(propan-2-yloxy)phenoxymethyl]-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol (48) (1.50 g, 66%) as a colourless oil.
後処理
- temperatureThe reaction was cooled to room temperature
- washwashed with water (200 mL)
- customThe solid material was removed by filtration
- customThe organic layer was separated
- dry with materialdried (Na2SO4)
- concentrationconcentrated
- customPurification by column chromatography on silica gel (Hexanes/EtOAc, 4:1)
出典と根拠
- ORDレコード
- ord-08f1a9d1c0844460a5e8342c80ff4fc6
- 出典データセット
- uspto-grants-2012_01
- 特許番号
- US08101605B2
関連ノート
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