ethyl (E)-3-(3-quinolinyl)acrylate → 3-(Quinolin-3-yl)prop-2-en-1-ol

HRID 2229241Notes

Reaction equation

[H-].C([Al+]CC(C)C)C(C)C.[N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[C:13](/[CH:21]=[CH:22]/[C:23](OCC)=[O:24])[CH:12]=1>C1(C)C=CC=CC=1.C(Cl)Cl>[N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[C:13](/[CH:21]=[CH:22]/[CH2:23][OH:24])[CH:12]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of diisobutylaluminum hydride in toluene (1.0M, 31 ml) was added dropwise to a solution of ethyl (E)-3-(3-quinolinyl)acrylate (2.94 g) in CH2Cl2 (50 ml) at −78° C. and the mixture was stirred at −78° C. for 30 minutes. The reaction mixture was washed with saturated aqueous solution of sodium potassium tartrate and brine, dried and concentrated. The residue was crystallized from CH2Cl2-ethyl acetate to give the titled compound (1.31 g) as a colorless solid.

Workup

washThe reaction mixture was washed with saturated aqueous solution of sodium potassium tartrate and brine
customdried
concentrationconcentrated
customThe residue was crystallized from CH2Cl2-ethyl acetate

Sources & evidence

ORD record: ord-ad6c749516f046efb22bb803ac7d8c84
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06420375B1

Reaction notes

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