Ethyl formate → 3,3-Bis(2-fluoro-4-methylphenyl)-2-(1-methyl-1H-tetrazol-5-yl)-2-propenal

HRID 974490

Reaction equation

HRID 974490 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]([C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=1[F:24])=[CH:10][C:11]1[N:15]([CH3:16])[N:14]=[N:13][N:12]=1.C([Li])CCC.[CH:30](OCC)=[O:31]>O1CCCC1>[F:24][C:18]1[CH:19]=[C:20]([CH3:23])[CH:21]=[CH:22][C:17]=1[C:9]([C:3]1[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=1[F:1])=[C:10]([C:11]1[N:15]([CH3:16])[N:14]=[N:13][N:12]=1)[CH:30]=[O:31]

Participants

5

Reactant 3

HCID 8025Ethyl formateHCID 147239931,1-Bis(2-fluoro-4-methylphenyl)-2-(1-methyl-1H-tetrazol-5-yl)etheneHCID 178418339Butyllithium

Product 1

HCID 147239943,3-Bis(2-fluoro-4-methylphenyl)-2-(1-methyl-1H-tetrazol-5-yl)-2-propenalYield 37.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1,1-bis(2-fluoro-4-methylphenyl)-2-(1-methyl-1H-tetrazol-5-yl)ethene (1.6 g, 5.0 mmoles) in tetrahydrofuran (20 mL) at -78° C. was added butyl lithium (2.3 mL of a 2.2M solution, 5 mmoles). After stirring for 15 minutes, ethyl formate (0.44 g, 6.0 mmoles) was added and the solution stirred with cooling for 2 hours. The reaction was quenched with 1N hydrochloric acid and the mixture extracted with diethyl ether. The extracts were dried (MgSO4) and evaporated. The residue was crystallized from isopropyl acetate to give 0.66 g of the title compound; m.p.=154°-155° C.

Workup

  1. stirringthe solution stirred
  2. temperaturewith cooling for 2 hours
  3. customThe reaction was quenched with 1N hydrochloric acid
  4. extractionthe mixture extracted with diethyl ether
  5. dry with materialThe extracts were dried (MgSO4)
  6. customevaporated
  7. customThe residue was crystallized from isopropyl acetate

Sources & evidence

ORD record
ord-7f15a6fce5ed4f7889a8a5312a6a3a25
Source dataset
uspto-grants-1991_11
Patent number
US05068346

Linked notes

Loading…