Phenethyltriphenylphosphonium bromide → HCID 86702773, compound

HRID 718527Notes

Reaction equation

HRID 718527 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.[C:34]([CH:39]1[CH2:44][CH2:43][CH:42]([CH2:45][CH:46]=O)[CH2:41][CH2:40]1)([CH2:37][CH3:38])([CH3:36])[CH3:35]>>[C:34]([CH:39]1[CH2:44][CH2:43][CH:42]([CH2:45][CH:46]=[CH:2][CH2:3][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:41][CH2:40]1)([CH2:37][CH3:38])([CH3:36])[CH3:35]

Participants

4

Reactant 3

HCID 10863251Phenethyltriphenylphosphonium bromideHCID 11333063[4-(2-Methylbutan-2-yl)cyclohexyl]acetaldehydeHCID 178418339Butyllithium

Product 1

HCID 86702773HCID 86702773, compoundYield 48.8%

Procedure

Starting from phenethyltriphenylphosphonium bromide (2.00 g, 4.47 mmol, 1.0 equiv.), n-BuLi (1.6 M in hexanes, 2.8 mL, 4.47 mmol, 1.0 equiv.) and 2-(4-tert-pentylcyclohexyl)acetaldehyde (1.32 g, 6.71 mmol, 1.5 equiv.), 0.62 g (48%) of the title compound as a colorless oil was obtained after purification by flash chromatography on SiO2 (cyclohexane).

Sources & evidence

ORD record
ord-9240ae214feb4f6d9a2582ed6f3e5ddc
Source dataset
uspto-grants-2015_11
Patent number
US09193935B2

Reaction notes

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