Water → 2-(1-Methylethyl)-5,9-dimethyl-2,4,8-decatrienenitrile

HRID 1464466

Reaction equation

C(OP([CH:9]([CH:12]([CH3:14])[CH3:13])[C:10]#[N:11])(OCC)=O)C.C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH3:25][C:26](=[CH:28][CH2:29][CH2:30]/[C:31](=[CH:33]/[CH:34]=O)/[CH3:32])[CH3:27].O>C1(C)C=CC=CC=1.CCCCCC.C(OCC)(=O)C>[CH3:14][CH:12]([C:9](=[CH:34][CH:33]=[C:31]([CH3:32])[CH2:30][CH2:29][CH:28]=[C:26]([CH3:27])[CH3:25])[C:10]#[N:11])[CH3:13]

Participants

Conditions

Temperature: -70 °C

Procedure

To a solution of 2-(diethylphosphono)isovaleronitrile (6.54 g, 30 mmol) in toluene (55 ml) was added a 0.5M solution of potassium bis(trimethylsilyl)amide in toluene (56 ml) with stirring on a cooling bath at -70° C. After 30 minutes, geranial (3.80 g, 25 mmol) was added thereto with continuous stirring at the same temperature, and then the reaction mixture was warmed up to room temperature. After addition of water to the mixture, the organic layer was extracted. The organic extract was washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride, dried over MgSO4, and filtered. The filtrate was concentrated to give a residue, which was then subjected to silica gel column chromatography (solvent: n-hexane/ethyl acetate=100:1) to give 2-(1-methylethyl)-5,9-dimethyl-2,4,8-decatrienenitrile (4.87 g, 90%, 2Z:2E=22.4:1).

Workup

stirringwith continuous stirring at the same temperature
temperaturethe reaction mixture was warmed up to room temperature
extractionthe organic layer was extracted
extractionThe organic extract
washwas washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
dry with materialdried over MgSO4
filtrationfiltered
concentrationThe filtrate was concentrated
customto give a residue, which

Sources & evidence

ORD record: ord-790ffec7d70b40f78fa3a297f878aad1
Source dataset: uspto-grants-1994_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05304661

Linked notes

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