3,7-Dimethyloctanal → HCID 86702758, compound

HRID 718508Notes

Reaction equation

HRID 718508 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.[CH3:34][CH:35]([CH2:39][CH2:40][CH2:41][CH:42]([CH3:44])[CH3:43])[CH2:36][CH:37]=O>>[CH3:34][CH:35]([CH2:39][CH2:40][CH2:41][CH:42]([CH3:44])[CH3:43])[CH2:36][CH:37]=[CH:2][CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 3

HCID 1107473,7-DimethyloctanalHCID 10863251Phenethyltriphenylphosphonium bromideHCID 178418339Butyllithium

Product 1

HCID 86702758HCID 86702758, compoundYield 55.1%

Procedure

Starting from phenethyltriphenylphosphonium bromide (3.85 g, 8.61 mmol, 1.0 equiv.), n-BuLi (1.6 M in hexanes, 5.4 mL, 8.61 mmol, 1.0 equiv.) and 3,7-dimethyloctanal (2.02 g, 12.9 mmol, 1.5 equiv.), 1.16 g (55%) of the title compound as a colorless oil was obtained after purification by flash chromatography on SiO2 (cyclohexane).

Sources & evidence

ORD record
ord-6f766b26a7a44141996d4eb59e0ee4e8
Source dataset
uspto-grants-2015_11
Patent number
US09193935B2

Reaction notes

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