Water → 2-(5-(3-Isopropylphenyl)hex-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.[CH:38]([C:41]1[CH:42]=[C:43]([CH:47]([CH3:51])[CH2:48][CH:49]=O)[CH:44]=[CH:45][CH:46]=1)([CH3:40])[CH3:39].O>C1COCC1>[CH:38]([C:41]1[CH:42]=[C:43]([CH:47]([CH3:51])[CH2:48][CH:49]=[C:12]([C:3]2[CH:4]=[CH:5][C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:2]=2)[CH3:13])[CH:44]=[CH:45][CH:46]=1)([CH3:40])[CH3:39]Participants
Conditions
- Temperature
- 0 °C
Procedure
A solution of 1-(2-naphthyl)ethyltriphenylphosphonium bromide (2.30 g, 4.62 mmol, 1.0 equiv.) in THF (16 mL), was cooled to 0° C. After adding n-BuLi (1.6 M in hexanes, 2.9 mL, 4.62 mmol, 1.0 equiv.) at 0° C., the red-brown suspension was stirred at 0° C. for 15 min. 3-(3-Isopropylphenyl)butanal (1.32 g, 6.94 mmol, 1.5 equiv.) in THF (2 mL) was added, and the mixture was stirred at 0° C.→70° C. for 18 h. After addition of H2O, the aqueous layer was extracted with hexanes (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 0.57 g (38%) of the title compound as a colorless viscous oil.
Workup
- stirringthe mixture was stirred at 0° C.→70° C. for 18 h
- extractionthe aqueous layer was extracted with hexanes (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)
Sources & evidence
- ORD record
- ord-a76cd79448e54099a83d70ce8b193d6b
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09193935B2
Reaction notes
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