Hydrochloric Acid → HCID 14539527, compound

HRID 330665Notes

Reaction equation

HRID 330665 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[CH:9][C:10]2[N:14]([CH3:15])[N:13]=[N:12][N:11]=2)=[CH:4][CH:3]=1.C([Li])CCC.[CH:28](OCC)=[O:29].Cl>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=2)=[C:9]([C:10]2[N:14]([CH3:15])[N:13]=[N:12][N:11]=2)[CH:28]=[O:29])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8025Ethyl formateHCID 14539528HCID 14539528, compoundHCID 178418339Butyllithium

Product 1

HCID 14539527HCID 14539527, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-80 °C

Procedure

To a finely divided suspension of 1,1-bis(4-fluorophenyl)-2-(1-methyl-1H-tetrazol-5-yl)ethene (1.0 g, 3.3 mmoles) [prepared in Step B] in tetrahydrofuran (10 mL) at -80° C. was added n-butyl lithium (1.54 mL of 2.14M solution), 3.3 mmoles) with the formation of a dark violet color. After stirring for 40 minutes at -80° C., ethyl formate (0.32 g, 4.3 mmoles) was added and the mixture stirred for 2.5 hours at -80° C. The mixture was hydrolyzed with 1N hydrochloric acid and extracted with methylene chloride. The extracts were dried (MgSO4) and evaporated in vacuo. The residue was triturated with diethyl ether to give 0.77 g of yellow solid, m.p. 128°-131° C. The solid was crystallized from isopropyl acetate-hexane to give 0.55 g of the title compound; m.p.=130°-132° C.

Workup

  1. stirringthe mixture stirred for 2.5 hours at -80° C
  2. extractionextracted with methylene chloride
  3. dry with materialThe extracts were dried (MgSO4)
  4. customevaporated in vacuo
  5. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-2b851fc289564695b6bb713b8f65e9be
Source dataset
uspto-grants-1990_01
Patent number
US04897490

Reaction notes

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