Ethyl formate → HCID 14723917, compound

HRID 330644Notes

Reaction equation

HRID 330644 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])=[C:18]([CH3:23])[CH:17]=2)=[CH:9][C:10]2[N:14]([CH3:15])[N:13]=[N:12][N:11]=2)=[CH:4][C:3]=1[CH3:24].C([Li])CCC.[CH:30](OCC)=[O:31]>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[C:18]([CH3:23])[CH:17]=2)=[C:9]([C:10]2[N:14]([CH3:15])[N:13]=[N:12][N:11]=2)[CH:30]=[O:31])=[CH:4][C:3]=1[CH3:24]

Participants

5

Reactant 3

HCID 8025Ethyl formateHCID 14723916HCID 14723916, compoundHCID 178418339Butyllithium

Product 1

HCID 14723917HCID 14723917, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 1,1-bis(4-fluoro-3-methylphenyl)-2-(1-methyltetrazol-5-yl)ethene (3.58 g, 11.0 mmoles)) in dry tetrahydrofuran (20 mL) at -78° C. was treated with n-butyllithium (5.3 ml of 2.5M solution in hexane; 13.25 mmoles) and the mixture stirred at -78° C. for 0.5 hours. Ethyl formate (1.33 ml; 1.22 g, 16.5 mmoles) was added and the mixture was allowed to warm up to 23° C. over 1 hour, then quenched with 2N HCl (250 mL). The aqueous phase was extracted with ethyl acetate (3×50 mL) and the combined organic layers were dried (MgSO4) and evaporated. The residue was purified by chromatography using 20% EtOAc-Hexane as eluent to afford 2.2 g (57%) of the title compound as a foam. MS (CI): m/e=355 for (M+H)+ ;

Workup

  1. temperatureto warm up to 23° C. over 1 hour
  2. customquenched with 2N HCl (250 mL)
  3. extractionThe aqueous phase was extracted with ethyl acetate (3×50 mL)
  4. dry with materialthe combined organic layers were dried (MgSO4)
  5. customevaporated
  6. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-12cfea5de91b4eff8a586bfd96f76fd7
Source dataset
uspto-grants-1990_01
Patent number
US04897490

Reaction notes

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