Acetic Acid → HCID 86742613, compound

HRID 414296Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7](/[C:10](/[C:16]([F:19])([F:18])[F:17])=[CH:11]\[C:12](OC)=[O:13])=[CH:6][CH:5]=1)[CH3:2].[H-].C([Al+]CC(C)C)C(C)C.C(O)(=O)C.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1(C)C=CC=CC=1.O>[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7](/[C:10](/[C:16]([F:17])([F:18])[F:19])=[CH:11]\[CH:12]=[O:13])=[CH:8][CH:9]=1)[CH3:2]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of methyl E-3-(4-ethoxyphenyl)-4,4,4-trifluorobut-2-enoate, prepared according to Example 17, stage 1, (1.5 g, 5.5×10-3 moles) in toluene (20 ml) at -78° C. was added dropwise one molar equivalent of diisobutylaluminium hydride (5.5 ml, 5.5×10-3 moles) in toluene. The resulting solution was stirred at -78° C. for two hours before quenching the reaction by the sequential addition of acetic acid (0.40 ml, 7.0×10-3 moles), water (1 ml) and sodium sulphate (10 g). The resulting slurry was allowed to warm to room temperature and after a further twenty minutes stirring the solids were filtered off through silica. After removal of the solvent the crude aldehyde was purified by silica chromatography (eluted with 10%, in petroleum ether to give the title compound (0.87 g, 65%).

Workup

custombefore quenching
customthe reaction
temperatureto warm to room temperature and after a further twenty minutes
stirringstirring the solids
filtrationwere filtered off through silica
customAfter removal of the solvent the crude aldehyde
customwas purified by silica chromatography (
washeluted with 10%, in petroleum ether

Sources & evidence

ORD record: ord-8ca8422bccc04f7cb5b052162c0797d2
Source dataset: uspto-grants-1988_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04791139

Reaction notes

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