Toluene → HCID 12093580, compound

HRID 853739Notes

Reaction equation

HRID 853739 reaction equation
[CH:1](=[C:4]1[CH2:8][CH2:7][CH2:6][C:5]1=[O:9])[CH2:2][CH3:3].B(F)(F)F.[CH2:14]=[CH:15][C:16](=C)[CH3:17].[C:19]1(C)C=CC=CC=1>>[CH2:15]([CH:16]1[C:4]2([C:5](=[O:9])[CH2:6][CH2:7][CH2:8]2)[CH2:1][CH:2]=[C:3]([CH3:19])[CH2:17]1)[CH3:14]

Participants

5

Reactant 4

HCID 1140Toluene2×HCID 6356Boron trifluorideHCID 6557IsopreneHCID 30161952-Propylidenecyclopentanone

Product 1

HCID 12093580HCID 12093580, compoundYield 103%

Procedure

A solution of propylidene cyclopentanone (124 g; 1 mol) in toluene (124 g) was cooled to 0° C. BF3 etherate (10 ml) were added at 0° C. over 10 minutes. Isoprene (168 g; 2.47 mol), dissolved in toluene (168 g) was then added dropwise over 3 hours at 0° C. Stirring was continued at 0° C. for 3.5 hours. Usual work-up (see above) afforded 198 g of a crude product as a mixture of isomer (ratio 5/4/91). Distillation through a Vigreux column afforded 165 g of 96% pure cycloadduct (yield: 86%).

Workup

  1. additionwas then added dropwise over 3 hours at 0° C

Sources & evidence

ORD record
ord-23f99187896046d7827f5bf25b8d1f4e
Source dataset
uspto-grants-2007_08
Patent number
US07256170B2

Reaction notes

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