4-(1,3-Benzodioxol-5-yl)-2-butanone → 5-(3-Methyl-5-phenylpent-3-enyl)benzo[d][1,3]dioxole

HRID 718516Notes

Reaction equation

HRID 718516 reaction equation
[Br-].[CH2:2]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Li]CCCC.[O:34]1[C:38]2[CH:39]=[CH:40][C:41]([CH2:43][CH2:44][C:45](=O)[CH3:46])=[CH:42][C:37]=2[O:36][CH2:35]1>>[CH3:46][C:45](=[CH:2][CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH2:44][CH2:43][C:41]1[CH:40]=[CH:39][C:38]2[O:34][CH2:35][O:36][C:37]=2[CH:42]=1

Participants

4

Reactant 3

HCID 620984-(1,3-Benzodioxol-5-yl)-2-butanoneHCID 10863251Phenethyltriphenylphosphonium bromideHCID 178418339Butyllithium

Product 1

HCID 679858275-(3-Methyl-5-phenylpent-3-enyl)benzo[d][1,3]dioxoleYield 30.7%

Procedure

Starting from phenethyltriphenylphosphonium bromide (1.82 g, 4.07 mmol, 1.0 equiv.), n-BuLi (1.6 M in hexanes, 2.6 mL, 4.07 mmol, 1.0 equiv.) and 4-(benzo[d][1,3]dioxol-5-yl)butan-2-one (1.17 g, 6.10 mmol, 1.5 equiv.), 0.35 g (30%) of the title compound as a colorless oil was obtained after purification by flash chromatography on SiO2 (cyclohexane/EtOAc 99:1).

Sources & evidence

ORD record
ord-67393ee1c683402babca401f3224ff50
Source dataset
uspto-grants-2015_11
Patent number
US09193935B2

Reaction notes

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