Methyl iodide → HCID 86701849, compound

HRID 1464893Notes

Reaction equation

[CH2:1]([C:5]1[CH2:10][CH:9]([CH3:11])[CH:8]([CH:12]=[O:13])[CH2:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].[CH3:14]C([O-])(C)C.[K+].CI>C(Cl)Cl>[CH2:1]([C:5]1[CH2:10][CH:9]([CH3:11])[C:8]([CH3:14])([CH:12]=[O:13])[CH2:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3]

Participants

Conditions

Temperature: -3 °C

Procedure

4-Isobutyl-6-methylcyclohex-3-enecarbaldehyde 3b (8 g, 44 mmol) was dissolved in methylene chloride (400 ml) and cooled to −3° C. with stirring and under nitrogen. KOtBu (6.7 g, 58 mmol) and MeI (19 g, 130 mmol) were added sequentially and the suspension stirred for 30 min before being allowed to return to room temperature. After stirring for a further 3 h the reaction crude was poured onto brine (400 ml), stirred for 10 min and the phases allowed to separate. The upper aqueous phase was extracted with methylene chloride (150 ml) and the organic phases combined, dried (Na2SO4) and concentrated in vacuo to give 8.5 g of an orange oil (8.5 g). The oil was purified by flash chromatography (MTBE/hexane 1:9) and combination of pure fractions gave 3c as a 7:3 mixture of diastereomers (7 g, colorless oil, 80% yield). 1 g of the oil was distilled to give a sample for olfactory assessment. (0.52 g, colourless oil, >99% pure).

Workup

stirringthe suspension stirred for 30 min
customto return to room temperature
stirringAfter stirring for a further 3 h
customthe reaction crude
additionwas poured onto brine (400 ml)
stirringstirred for 10 min
customto separate
extractionThe upper aqueous phase was extracted with methylene chloride (150 ml)
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-f0c66e45f9c7415f904df9a6d9e8ad36
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08999914B2

Reaction notes

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