N-isobutyl acetamidotriphenylphosphonium chloride → N-isobutyl 7-(4'-bromophenyl)-(2E)-hepten-6-ynamide

HRID 2106876Notes

Reaction equation

HRID 2106876 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][CH2:10][CH2:11][CH:12]=O)=[CH:4][CH:3]=1.[Cl-].[CH2:15]([N:19]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:20](=[O:22])[CH3:21])[CH:16]([CH3:18])[CH3:17]>>[CH2:15]([NH:19][C:20](=[O:22])/[CH:21]=[CH:12]/[CH2:11][CH2:10][C:9]#[C:8][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)[CH:16]([CH3:18])[CH3:17]

Participants

3

Reactant 2

HCID 23049290N-isobutyl acetamidotriphenylphosphonium chlorideHCID 230493415-(4'-Bromophenyl)-4-pentyn-1-al

Product 1

HCID 23049311N-isobutyl 7-(4'-bromophenyl)-(2E)-hepten-6-ynamide

Procedure

N-isobutyl 7-(4'-bromophenyl)-(2E)-hepten-6-ynamide was prepared from 5-(4'-bromophenyl)-4-pentyn-1-al and N-isobutyl acetamidotriphenylphosphonium chloride as in Example 9 and semi-hydrogenated as in Example 9 to give N-isobutyl 7-(4'-bromophenyl)-(2E,6Z)-hepta-dienamide.

Sources & evidence

ORD record
ord-374f2a5b94d040caaf34408244464c3c
Source dataset
uspto-grants-1990_06
Patent number
US04931469

Reaction notes

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