Diisobutylaluminumhydride → (trans)-3-[3-(6-Phenyl-1,3,5-hexatriynyl)oxiranyl]-2-propen-1-ol

HRID 1906981Notes

Reaction equation

[H-].C([Al+]CC(C)C)C(C)C.[C:11]1([C:17]#[C:18][C:19]#[C:20][C:21]#[C:22][C@@H:23]2[O:25][C@H:24]2[CH:26]=[CH:27][CH:28]=[O:29])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C1(C)C=CC=CC=1.O1CCCC1>[C:11]1([C:17]#[C:18][C:19]#[C:20][C:21]#[C:22][C@@H:23]2[O:25][C@H:24]2[CH:26]=[CH:27][CH2:28][OH:29])[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Diisobutylaluminum hydride (0.35 ml of a 1.76M solution in toluene, 0.61 mmole) was added dropwise to a stirred -78° C. solution of (trans)-3-[3-(6-phenyl-1,3,5-hexatriynyl)oxiranyl]-2-propenal (50 mg, 0.20 mmole; see example 5) in 6 ml of dry tetrahydrofuran. The mixture was stirred for 2 hours at -78° C. and was then quenched at that temperature by the dropwise addition of ca. 0.5 ml of a solution of methanol-acetic acid 4:1. The mixture was warmed to room temperature, water was added and the mixture was extracted with ether. The combined ether extracts were washed with water and saturated aqueous sodium chloride and were dried over anhydrous magnesium sulfate. Removal of solvent gave an oil which was purified by preparative thin layer chromatography (ethyl acetate-hexane 1:1) to afford 34 mg pure title compound, melting point 65°-66° C.

Workup

customwas then quenched at that temperature by the dropwise addition of ca. 0.5 ml of a solution of methanol-acetic acid 4:1
temperatureThe mixture was warmed to room temperature
additionwater was added
extractionthe mixture was extracted with ether
washThe combined ether extracts were washed with water and saturated aqueous sodium chloride
dry with materialwere dried over anhydrous magnesium sulfate
customRemoval of solvent
customgave an oil which
customwas purified by preparative thin layer chromatography (ethyl acetate-hexane 1:1)

Sources & evidence

ORD record: ord-7f481c3f15324a78a5323c872b1ad98a
Source dataset: uspto-grants-1987_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04654426

Reaction notes

Loading…