(E)-(2-formyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)acetonitrile → (E)-[2-(1-hydroxybutyl)-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene]acetonitrile

HRID 452158Notes

Reaction equation

HRID 452158 reaction equation
[CH:1]([C:3]1[CH:20]=[CH:19][C:6]2/[C:7](=[CH:16]/[C:17]#[N:18])/[C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[CH2:10][CH2:11][C:5]=2[CH:4]=1)=[O:2].[CH2:21]([Mg]Br)[CH2:22][CH3:23]>>[OH:2][CH:1]([C:3]1[CH:20]=[CH:19][C:6]2/[C:7](=[CH:16]/[C:17]#[N:18])/[C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[CH2:10][CH2:11][C:5]=2[CH:4]=1)[CH2:21][CH2:22][CH3:23]

Participants

3

Reactant 2

HCID 86656742(E)-(2-formyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)acetonitrileHCID 178455851HCID 178455851, compound

Product 1

HCID 67210524(E)-[2-(1-hydroxybutyl)-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene]acetonitrileYield 64%

Procedure

[step 1] Using (E)-(2-formyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)acetonitrile (245 mg, 0.95 mmol) obtained in Example 83, step 1, and propylmagnesium bromide (2.0 mol/L THF solution; 0.71 mL, 1.42 mmol) instead of methylmagnesium chloride, and in the same manner as in Example 83, step 2, (E)-[2-(1-hydroxybutyl)-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene]acetonitrile (184 mg, 64%) was obtained.

Sources & evidence

ORD record
ord-d2ebebfa00f54a5d88e356ceaa4e9f93
Source dataset
uspto-grants-2013_07
Patent number
US08486980B2

Reaction notes

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