Water → 5-(4-(3-Isopropylphenyl)pent-1-enyl)benzo[d][1,3]dioxole
Reaction equation
[Br-].[O:2]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)=[CH:10][C:5]=2[O:4][CH2:3]1.[Li]CCCC.[CH:36]([C:39]1[CH:40]=[C:41]([CH:45]([CH3:49])[CH2:46][CH:47]=O)[CH:42]=[CH:43][CH:44]=1)([CH3:38])[CH3:37].O>C1COCC1>[CH:36]([C:39]1[CH:40]=[C:41]([CH:45]([CH3:49])[CH2:46][CH:47]=[CH:11][C:9]2[CH:8]=[CH:7][C:6]3[O:2][CH2:3][O:4][C:5]=3[CH:10]=2)[CH:42]=[CH:43][CH:44]=1)([CH3:38])[CH3:37]Participants
6
Conditions
- Temperature
- 0 °C
Procedure
A solution of (benzo[d][1,3]dioxol-5-ylmethyl)triphenylphosphonium bromide (4.77 g, 10.0 mmol, 1.0 equiv.) in THF (20 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 dark red suspension was stirred at 0° C. for 10 min. 3-(3-Isopropylphenyl)butanal (1.90 g, 10.0 mmol, 1.0 equiv.) in THF (10 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 and MTBE, the combined organic phases were dried (MgSO4), filtered and the filtrate was concentrated. The residue was purified by flash chromatography on SiO2 (hexanes/EtOAc 4:1) to yield 2.35 g (75%) of the title compound as a yellow oil.
Workup
- stirringthe mixture was stirred at 0° C.→25° C. for 16 h
- extractionthe aqueous layer was extracted with hexanes and MTBE
- 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 4:1)
Sources & evidence
- ORD record
- ord-9d733e36c8b14f94b8fe3ac8e3578bca
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09193935B2
Reaction notes
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