Dimethylformamide → (E,E,E)-2-(6,6-dimethyl-2-hepten-4-ynyl)-8-[3-[3-thienyl)phenyl]-2,7-octadienic acid methyl ester

HRID 1757266Notes

Reaction equation

HRID 1757266 reaction equation
S1C=[CH:4][C:3]([C:6]2[CH:7]=[C:8]([CH:16]=[CH:17][CH:18]=2)OCCCCC#N)=[CH:2]1.S1C=CC(C2C=[C:26]([OH:30])C=CC=2)=C1.Br[CH2:32]CCCC#N.[H-].[Na+].[S:40]1[CH:44]=[CH:43][C:42]([C:45]2[CH:46]=[C:47](/[CH:51]=[CH:52]/[CH2:53][CH2:54][CH2:55][C:56]#N)[CH:48]=[CH:49][CH:50]=2)=[CH:41]1.CN(C)[CH:60]=[O:61]>>[CH3:26][O:30][C:60](=[O:61])/[C:18](/[CH2:17]/[CH:16]=[CH:8]/[C:7]#[C:6][C:3]([CH3:2])([CH3:4])[CH3:32])=[CH:56]/[CH2:55][CH2:54][CH2:53]/[CH:52]=[CH:51]/[C:47]1[CH:48]=[CH:49][CH:50]=[C:45]([C:42]2[CH:43]=[CH:44][S:40][CH:41]=2)[CH:46]=1

Participants

7

Reactant 6

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 794355-BromopentanenitrileHCID 41303433-(Thiophen-3-YL)phenolHCID 193901545-[3-(3-Thienyl)phenoxy]valeronitrileHCID 19390157HCID 19390157, compound

Product 1

HCID 15288593(E,E,E)-2-(6,6-dimethyl-2-hepten-4-ynyl)-8-[3-[3-thienyl)phenyl]-2,7-octadienic acid methyl ester

Procedure

(E,E)-2-(6,6-dimethyl-2-hepten-4-ynyl)-7-[3-(3-thienyl)phenoxy]-2-heptenoic acid methyl ester is obtained by carrying out the same reactions as in Referential Example 1 except that 5-[3-(3-thienyl)phenoxy]valeronitrile [synthesized by condensing 3-(3-thienyl)phenol with 5-bromovaleronitrile in dimethylformamide in the presence of sodium hydride] is used in place of (E)-6-[3-(3-thienyl)phenyl]-5-hexenenitrile which is the raw material compound used in the above.

Sources & evidence

ORD record
ord-41556c49247e4e76bfb432fc041fb349
Source dataset
uspto-grants-1995_08
Patent number
US05444084

Reaction notes

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