Formic Acid → HCID 178520938, compound

HRID 2399214Notes

Reaction equation

HRID 2399214 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[C:15][CH:16]3[CH2:21][CH2:20][C:19](=[CH:22][O:23]C)[CH2:18][CH2:17]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(O)=O>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[C:15][C@H:16]3[CH2:21][CH2:20][C@H:19]([CH:22]=[O:23])[CH2:18][CH2:17]3)=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 19386507HCID 19386507, compound

Product 1

HCID 178520938HCID 178520938, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 0.95 g of 4'-fluoro-4-[[4-(methoxymethylidene)cyclohexyl]ethynyl]biphenyl in 40 ml of toluene was treated with 4 ml of formic acid and stirred at room temperature overnight. The formic acid phase was separated and the toluene phase was washed neutral with water, dried over sodium sulphate, filtered and concentrated. For the ring isomerization, the resulting crude 4-[(4'-fluoro-4-biphenylyl)ethynyl]cyclohexanecarboxaldehyde was dissolved in 35 ml of ethanol, treated with 8.2 ml of 0.1N alcoholic potassium hydroxide solution and stirred at room temperature for 2 hours. The reaction mixture was diluted with diethyl ether, washed with saturated sodium hydrogen carbonate solution and with water, dried over sodium sulphate, filtered and concentrated. 0.80 g of trans-4-[(4'-fluoro-4-biphenylyl)ethynyl]cyclohexanecarboxaldehyde was obtained.

Workup

  1. customThe formic acid phase was separated
  2. washthe toluene phase was washed neutral with water
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutionFor the ring isomerization, the resulting crude 4-[(4'-fluoro-4-biphenylyl)ethynyl]cyclohexanecarboxaldehyde was dissolved in 35 ml of ethanol
  7. additiontreated with 8.2 ml of 0.1N alcoholic potassium hydroxide solution
  8. stirringstirred at room temperature for 2 hours
  9. additionThe reaction mixture was diluted with diethyl ether
  10. washwashed with saturated sodium hydrogen carbonate solution and with water
  11. dry with materialdried over sodium sulphate
  12. filtrationfiltered
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-d9029f88e9a743cbb9629a50fa1911a2
Source dataset
uspto-grants-1995_09
Patent number
US05447657

Reaction notes

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