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

HRID 452180Notes

Reaction equation

C[O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2=[C:9]([CH:23]=1)[O:10][CH2:11][C:12]1[CH:22]=[CH:21][CH:20]=[CH:19][C:13]=1/[C:14]/2=[C:15](/[C:17]#[N:18])\[CH3:16])=O.[BH4-].[Li+].Cl>C1COCC1>[OH:2][CH2:3][C:5]1[CH:6]=[CH:7][C:8]2=[C:9]([CH:23]=1)[O:10][CH2:11][C:12]1[CH:22]=[CH:21][CH:20]=[CH:19][C:13]=1/[C:14]/2=[C:15](\[CH3:16])/[C:17]#[N:18]

Participants

Conditions

Temperature: 50 °C

Procedure

[step 2] (Z)-11-(1-Cyanoethylidene)-6,11-dihydrodibenzo[b,e]oxepine-3-carboxylic acid methyl ester (0.557 g, 1.82 mmol) was suspended in THF (9 mL), lithium borohydride (0.199 g, 9.12 mmol) was added and the mixture was stirred at 50° C. for 8 hr. To the mixture was added ice, and the mixture was neutralized to pH 2 with 1 mol/L hydrochloric acid, and extracted twice with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Isopropyl alcohol (13 mL) was added to the residue, and the mixture was filtered to give the title compound (0.364 g, 72%).

Workup

additionTo the mixture was added ice
extractionextracted twice with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
additionIsopropyl alcohol (13 mL) was added to the residue
filtrationthe mixture was filtered

Sources & evidence

ORD record: ord-4f46ef74df224838bf8514196648345c
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08486980B2

Reaction notes

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