Acetic Acid → 5-(4-(4-Methoxyphenyl)-3-methylbut-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.[CH3:31][O:32][C:33]1[CH:38]=[CH:37][C:36]([CH2:39][CH:40]([CH3:43])[CH:41]=O)=[CH:35][CH:34]=1.CC(O)=O>C1COCC1>[CH3:31][O:32][C:33]1[CH:38]=[CH:37][C:36]([CH2:39][CH:40]([CH3:43])[CH:41]=[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:35][CH:34]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
Potassium t-pentylat (1.7 M in toluene, 6.5 mL, 11.0 mmol, 1.1 equiv.) was added to 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) at 25° C. After the dark red suspension was stirred at 25° C. for 15 min, 3-(4-methoxyphenyl)-2-methylpropanal (1.78 g, 10.0 mmol, 1.0 equiv.) in THF (10 mL) was added, and the mixture was stirred at 70° C. for 1.5 h. After addition of 20% aq. AcOH-solution (10 mL) at 25° C., the aqueous layer was extracted with 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 19:1) to yield 2.20 g (74%) of the title compound as a yellow oil.
Workup
- stirringthe mixture was stirred at 70° C. for 1.5 h
- extractionthe aqueous layer was extracted with 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 19:1)
Sources & evidence
- ORD record
- ord-6131910f8b824feba0b27f5c68ea8b00
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09193935B2
Reaction notes
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