3,3-Bis(4-fluorophenyl)-2-[1-(1-methylethyl)-1H-tetrazol-5-yl]-2-propenal → 5,5-bis(4-fluorophenyl)-4-[2-(1-methylethyl)-2H-tetrazol-5-yl]-2,4-pentadienal

HRID 974458Notes

Reaction equation

HRID 974458 reaction equation
FC1C=CC([C:8](C2C=CC(F)=CC=2)=[C:9](C2N(C(C)C)N=NN=2)[CH:10]=[O:11])=CC=1.[F:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]([C:46]2[CH:51]=[CH:50][C:49]([F:52])=[CH:48][CH:47]=2)=[C:35]([C:38]2[N:39]=[N:40][N:41]([CH:43]([CH3:45])[CH3:44])[N:42]=2)C=O)=[CH:30][CH:29]=1>>[F:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]([C:46]2[CH:51]=[CH:50][C:49]([F:52])=[CH:48][CH:47]=2)=[C:35]([C:38]2[N:39]=[N:40][N:41]([CH:43]([CH3:44])[CH3:45])[N:42]=2)[CH:8]=[CH:9][CH:10]=[O:11])=[CH:30][CH:29]=1

Participants

3

Reactant 2

HCID 147238733,3-Bis(4-fluorophenyl)-2-[1-(1-methylethyl)-1H-tetrazol-5-yl]-2-propenalHCID 147238743,3-Bis(4-fluorophenyl)-2-[2-(1-methylethyl)-2H-tetrazol-5-yl]-2-propenal

Product 1

HCID 545613945,5-bis(4-fluorophenyl)-4-[2-(1-methylethyl)-2H-tetrazol-5-yl]-2,4-pentadienalYield 82%

Procedure

The general procedure of Example 23, Step A was repeated, except that the 3,3-bis(4-fluorophenyl)-2-[1-(1-methylethyl)-1H-tetrazol-5-yl]-2-propenal utilized therein was replaced by 3,3-bis(4-fluorophenyl)-2-[2-(1-methylethyl)-2H-tetrazol-5-yl]-2-propenal and there was thereby produced mostly 5,5-bis(4-fluorophenyl)-4-[2-(1-methylethyl)-2H-tetrazol-5-yl]-2,4-pentadienal in 82% yield; MS (CI): m/e=381 for (M+H)+. This product was then subjected to the general procedure of Example 23, Step B and there was thereby produced ethyl 9,9-bis(4-fluorophenyl)-5-hydroxy-8-[2-(1-methylethyl)-2H-tetrazol-5-yl]-3-oxo-6,8-nonadienoate containing some inseparable ethyl 7,7-bis(4-fluorophenyl)-5-hydroxy-6-[2-(2-(1-methylethyl)-2H-tetrazol-5-yl]-3-oxo-6-heptenoate in 69.7% yield.

Sources & evidence

ORD record
ord-7723b963ec6449dd9def4dfe2fcc92de
Source dataset
uspto-grants-1991_11
Patent number
US05068346

Reaction notes

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