Water → 1-Methyl-4-(4-methyltridec-2-enyl)benzene
反応式
[Br-].[CH3:2][C:3]1[CH:29]=[CH:28][C:6]([CH2:7][CH2:8][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:5][CH:4]=1.[Li]CCCC.[CH3:35][CH:36]([CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[CH:37]=O.O>C1COCC1>[CH3:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][CH:8]=[CH:35][CH:36]([CH3:37])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])=[CH:28][CH:29]=1参加物
6
反応条件
- 温度
- 65 °C
実験手順
p-Methylphenethyltriphenylphosphonium bromide (2.90 g, 6.29 mmol, 1.0 equiv.) in THF (12 mL), was cooled to 0° C. After adding n-BuLi (1.6 M in hexanes, 3.9 mL, 6.29 mmol, 1.0 equiv.) at 0° C., the red solution was stirred at 65° C. for 1 h. The mixture was re-cooled to 0° C., 2-methylundecanal (1.74 g, 9.43 mmol, 1.5 equiv.) in THF (5 mL) was added, and the mixture was stirred at 65° C. for 16 h. After addition of H2O, the aqueous layer was extracted with cyclohexane (2×), the combined organic phases were washed with brine, dried (MgSO4), filtered and the filtrate was concentrated. The residue was purified by flash chromatography on SiO2 (cyclohexane/EtOAc 997:3) to yield 1.24 g (69%) of the title compound as a colorless oil.
後処理
- temperatureThe mixture was re-cooled to 0° C.
- stirringthe mixture was stirred at 65° C. for 16 h
- extractionthe aqueous layer was extracted with cyclohexane (2×)
- washthe combined organic phases were washed with brine
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationthe filtrate was concentrated
- customThe residue was purified by flash chromatography on SiO2 (cyclohexane/EtOAc 997:3)
出典と根拠
- ORDレコード
- ord-7a8fd12443c4426792820d4950106c9c
- 出典データセット
- uspto-grants-2015_11
- 特許番号
- US09193935B2
反応ノート
読み込み中…