HCID 67210917, compound → HCID 67210517, compound

HRID 452198Notes

Reaction equation

HRID 452198 reaction equation
[C:1](/[C:3](=[C:7]1/[C:8]2[CH:27]=[CH:26][CH:25]=[CH:24][C:9]=2[O:10][CH2:11][C:12]2[CH:17]=[C:16]([C:18](OCCC)=[O:19])[CH:15]=[CH:14][C:13]/1=2)/[CH2:4][CH2:5][CH3:6])#[N:2].C(/C(=C1\C2C=CC=CC=2OCC2C=C(C(OCCC)=O)C=CC\1=2)/CCC)#N.C(C1(/C=C2\C3C=CC=CC=3OCC3C=C(C(OCCC)=O)C=CC\2=3)CC1)#N>>[OH:19][CH2:18][C:16]1[CH:15]=[CH:14][C:13]2/[C:7](=[C:3](/[CH2:4][CH2:5][CH3:6])\[C:1]#[N:2])/[C:8]3[CH:27]=[CH:26][CH:25]=[CH:24][C:9]=3[O:10][CH2:11][C:12]=2[CH:17]=1

Participants

4

Reactant 3

HCID 67210917HCID 67210917, compoundHCID 67210965HCID 67210965, compoundHCID 67211328HCID 67211328, compound

Product 1

HCID 67210517HCID 67210517, compoundYield 41%

Procedure

[step 1] Using pentanenitrile (2.7 mL, 25.9 mol) instead of cyclopropylacetonitrile, and in the same manner as in Reference Example B9, step 1, (E)-2-(8-bromo-6,11-dihydrodibenzo[b,e]oxepin-11-ylidene)pentanenitrile and (Z)-2-(8-bromo-6,11-dihydrodibenzo[b,e]oxepin-11-ylidene)pentanenitrile (1.90 g, 51%) were obtained. [step 2] Using (E)-2-(8-bromo-6,11-dihydrodibenzo[b,e]oxepin-11-ylidene)pentanenitrile and (Z)-2-(8-bromo-6,11-dihydrodibenzo[b,e]oxepin-11-ylidene)pentanenitrile (1.9 g, 5.37 mmol) obtained in Reference Example B11, step 1, instead of (E)-2-(8-bromo-6,11-dihydrodibenzo[b,e]oxepin-11-ylidene)cyclopropylacetonitrile and (Z)-2-(8-bromo-6,11-dihydrodibenzo[b,e]oxepin-11-ylidene)cyclopropylacetonitrile, and in the same manner as in Reference Example B9, step 2, propyl(E)-11-(1-cyanobutylidene)-6,11-dihydrodibenzo[b,e]oxepine-8-carboxylate and propyl(Z)-11-(1-cyanobutylidene)-6,11-dihydrodibenzo[b,e]oxepine-8-carboxylate (1.05 g, 54%) were obtained. [step 3] Using propyl(E)-11-(1-cyanobutylidene)-6,11-dihydrodibenzo[b,e]oxepine-8-carboxylate and propyl(Z)-11-(1-cyanobutylidene)-6,11-dihydrodibenzo[b,e]oxepine-8-carboxylate (1.05 g, 2.91 mmol) instead of propyl(E)-11-(1-cyanocyclopropylmethylene)-6,11-dihydrodibenzo[b,e]oxepine-8-carboxylate and propyl(Z)-11-(1-cyanocyclopropylmethylene)-6,11-dihydrodibenzo[b,e]oxepine-8-carboxylate, and in the same manner as in Example B9, step 3, (E)-2-(8-hydroxymethyl-6,11-dihydrodibenzo[b,e]oxepin-11-ylidene)pentanenitrile (0.370 g, 41%) was obtained.

Sources & evidence

ORD record
ord-7ec3ad9eb35b499cbc6c3250bf457dd0
Source dataset
uspto-grants-2013_07
Patent number
US08486980B2

Reaction notes

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