Hydrochloric Acid → (E)-2-(3-hydroxymethyl-6,11-dihydrodibenzo[b,e]oxepin-11-ylidene)propiononitrile

HRID 885428Notes

Reaction equation

[C:1](/[C:3](=[C:5]1/[C:6]2[CH:19]=[CH:18][C:17]([C:20](OC)=[O:21])=[CH:16][C:7]=2[O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]/1=2)/[CH3:4])#[N:2].[BH4-].[Li+].Cl>C1COCC1>[OH:21][CH2:20][C:17]1[CH:18]=[CH:19][C:6]2=[C:7]([CH:16]=1)[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1/[C:5]/2=[C:3](/[CH3:4])\[C:1]#[N:2]

Participants

Conditions

Temperature: 50 °C

Procedure

[step 2] Methyl (E)-11-(1-cyanoethylidene)-6,11-dihydrodibenzo[b,e]oxepine-3-carboxylate (6.40 g, 21.0 mmol) was suspended in THF (105 mL), and the solution was added with lithium borohydride (2.29 g, 105 mmol), followed by stirring at 50° C. for 6 hr. Ice was added to the reaction mixture, and the mixture was neutralized with 1 mol/L hydrochloric acid to pH 2, and extracted twice with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=30:70) to give the title compound (4.89 g, 17.6 mmol, 84.1%).

Workup

additionIce was added to the reaction mixture
extractionextracted twice with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=30:70)

Sources & evidence

ORD record: ord-0110254c19664b02be618077ad08f718
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08242151B2

Reaction notes

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