Florhydral → 1-Isopropyl-3-(6-phenylhex-4-en-2-yl)benzene

HRID 718513Notes

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.[CH:34]([C:37]1[CH:38]=[C:39]([CH:43]([CH3:47])[CH2:44][CH:45]=O)[CH:40]=[CH:41][CH:42]=1)([CH3:36])[CH3:35]>>[CH:34]([C:37]1[CH:42]=[CH:41][CH:40]=[C:39]([CH:43]([CH2:44][CH:45]=[CH:2][CH2:3][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH3:47])[CH:38]=1)([CH3:36])[CH3:35]

Participants

Reactant 3

HCID 86209Florhydral

HCID 10863251Phenethyltriphenylphosphonium bromide

HCID 178418339Butyllithium

Product 1

HCID 867027621-Isopropyl-3-(6-phenylhex-4-en-2-yl)benzeneYield 82%

Procedure

Starting from phenethyltriphenylphosphonium bromide (5.00 g, 11.2 mmol, 1.0 equiv.), n-BuLi (1.6 M in hexanes, 7.0 mL, 11.2 mmol, 1.0 equiv.) and 3-(3-isopropylphenyl)butanal (3.20 g, 16.8 mmol, 1.5 equiv.), 2.54 g (82%) of the title compound as a colorless oil was obtained after purification by flash chromatography on SiO2 (cyclohexane/EtOAc 997:3).

Sources & evidence

ORD record: ord-1bb95b518ad444989c97e3410708c034
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193935B2

Reaction notes

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