3,5,5-Trimethylhexanal → 2-(5.7.7-Trimethyloct-2-en-2-yl)naphthalene
Reaction equation
[Br-].[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH:12]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH3:13].[Li]CCCC.[CH3:38][CH:39]([CH2:43][C:44]([CH3:47])([CH3:46])[CH3:45])[CH2:40][CH:41]=O>>[CH3:38][CH:39]([CH2:43][C:44]([CH3:47])([CH3:46])[CH3:45])[CH2:40][CH:41]=[C:12]([C:3]1[CH:4]=[CH:5][C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:2]=1)[CH3:13]Participants
4
Conditions
- Temperature
- 25 °C
Procedure
Starting from (1-(2-naphthyl)ethyltriphenylphosphonium bromide (2.80 g, 5.63 mmol, 1.0 equiv.), n-BuLi (1.6 M in hexanes, 3.5 mL, 5.63 mmol, 1.0 equiv.) and 3,5,5-trimethylhexanal (1.20 g, 8.44 mmol, 1.5 equiv.), and after stirring the mixture at 25° C. for 3 h, 0.73 g (46%) of the title compound as a colorless oil was obtained after purification by flash chromatography on SiO2 (cyclohexane/EtOAc 997:3).
Sources & evidence
- ORD record
- ord-c8b157e8fa2a484eaa8601c93efd8daf
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09193935B2
Reaction notes
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