Hexane → HCID 69967781, compound

HRID 1955808Notes

Reaction equation

[C:1]1([Li])C=CC=C[CH:2]=1.C1CCCCC1.CCOCC.[C:19]1([CH2:25][O:26][C:27]2[CH:34]=[CH:33][C:30]([CH:31]=O)=[CH:29][C:28]=2[N+:35]([O-:37])=[O:36])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CCCCCC>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C.C1COCC1>[C:19]1([CH2:25][O:26][C:27]2[CH:34]=[CH:33][C:30]([CH:31]=[CH:1][CH3:2])=[CH:29][C:28]=2[N+:35]([O-:37])=[O:36])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a stirred suspension of (ethyl)triphenylphosphonium bromide (63.3 g, 170.5 mmol) in 270 mL of dry THF under Ar at 20° C., was added 91 mL of 1.8M phenyllithium in 70% cyclohexane/Et2O solution (163 mmol). After 30 minutes the reaction was cooled to -78° C., and a solution of 4-phenylmethoxy-3-nitrobenzaldehyde (38.96 g, 151.6 mmol) in 138 mL of THF was added by cannula over 25 minutes. The reaction was maintained at -78° C. for 60 minutes and stirred at 20° C. overnight prior to addition of 400 mL hexane. The supernatant was decanted and the solids stirred twice with additional THF/hexane which was also decanted. After concentration of the combined supernatants, the title compound (11.33 g, 1:1 trans to cis ratio) was eluted from silica gel by 0% to 25% EtOAc/hexane.

Workup

temperatureThe reaction was maintained at -78° C. for 60 minutes
customThe supernatant was decanted
stirringthe solids stirred twice with additional THF/hexane which
customwas also decanted
washAfter concentration of the combined supernatants, the title compound (11.33 g, 1:1 trans to cis ratio) was eluted from silica gel by 0% to 25% EtOAc/hexane

Sources & evidence

ORD record: ord-d31544b47d6440308cfcd77d6339511e
Source dataset: uspto-grants-1998_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05776983

Reaction notes

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