Imidazole → HCID 178455774, compound

HRID 2039355Notes

Reaction equation

[CH:1]([C@H:3]1[CH2:8][CH2:7][C@H:6]([CH2:9]O)[CH2:5][CH2:4]1)=[CH2:2].N1C=CN=C1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:35]I>C1(C)C=CC=CC=1>[I:35][CH2:9][C@H:6]1[CH2:7][CH2:8][C@H:3]([CH:1]=[CH2:2])[CH2:4][CH2:5]1

Participants

Conditions

Temperature: 5 °C

Procedure

Under a nitrogen atmosphere, (trans-4-vinyl cyclohexyl) methanol (7) (12.0 g), imidazole (7.6 g), and triphenylphosphine (Ph3P) (29.2 g) were put in toluene (200 ml) and stirred at 5° C. Iodine (27.2 g) was divided into 10 parts and added thereto in the temperature range of 5 to 10° C., and then stirred for another 3 hours . Completion of the reaction was confirmed by means of gas chromatographic analysis. The deposit was removed from the reaction mixture obtained by filtration, and the solvent was distilled off from the filtrate under reduced pressure. The residue obtained was purified with a fractional operation by means of column chromatography using heptane as the eluent and silica gel as the stationary phase powder, and dried, giving 15.2 g of 1-iodomethyl-trans-4-vinylcyclohexane (8). The yield based on the compound (7) was 71.0%.

Workup

additionadded
stirringin the temperature range of 5 to 10° C., and then stirred for another 3 hours
customThe deposit was removed from the reaction mixture
customobtained by filtration
distillationthe solvent was distilled off from the filtrate under reduced pressure
customThe residue obtained
customwas purified with a fractional operation by means of column chromatography
customdried

Sources & evidence

ORD record: ord-b62fb023494141d59dae2696b8c115f3
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08580142B2

Reaction notes

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