Water → 4-(4-(3-Isopropylphenyl)pent-1-enyl)-1,2-dimethoxybenzene
Reaction equation
[Br-].[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH2:12][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11].[Li]CCCC.[CH:37]([C:40]1[CH:41]=[C:42]([CH:46]([CH3:50])[CH2:47][CH:48]=O)[CH:43]=[CH:44][CH:45]=1)([CH3:39])[CH3:38].O>C1COCC1>[CH:37]([C:40]1[CH:41]=[C:42]([CH:46]([CH3:50])[CH2:47][CH:48]=[CH:12][C:6]2[CH:7]=[CH:8][C:9]([O:10][CH3:11])=[C:4]([O:3][CH3:2])[CH:5]=2)[CH:43]=[CH:44][CH:45]=1)([CH3:39])[CH3:38]Participants
6
Conditions
- Temperature
- 0 °C
Procedure
A solution of (3,4-dimethoxyphenyl)methyltriphenylphosphonium bromide (4.93 g, 10.0 mmol, 1.0 equiv.) in THF (10 mL), was cooled to 0° C. After adding n-BuLi (1.6 M in hexanes, 6.3 mL, 10.0 mmol, 1.0 equiv.) at 0° C., the red suspension was stirred at 0° C. for 20 min. 3-(3-Isopropylphenyl)butanal (2.09 g, 11.0 mmol, 1.1 equiv.) in THF (11 mL) was added, and the mixture was stirred at 0° C.→25° C. for 16 h. After addition of H2O at 25° C., the aqueous layer was extracted with hexanes (2×), the combined organic phases were dried (MgSO4), filtered and the filtrate was concentrated. The residue was purified by flash chromatography on SiO2 (hexanes/EtOAc 99:1→4:1) to yield 2.67 g (82%) of the title compound as a colorless oil.
Workup
- stirringthe mixture was stirred at 0° C.→25° C. for 16 h
- extractionthe aqueous layer was extracted with hexanes (2×)
- dry with materialthe combined organic phases were dried (MgSO4)
- filtrationfiltered
- concentrationthe filtrate was concentrated
- customThe residue was purified by flash chromatography on SiO2 (hexanes/EtOAc 99:1→4:1)
Sources & evidence
- ORD record
- ord-70aa7b1a48ce4de8b2d0c96872d3c431
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09193935B2
Reaction notes
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