Hydrochloric Acid → HCID 14890664, compound

HRID 1086319Notes

Reaction equation

HRID 1086319 reaction equation
[C:1]([C:3](=[C:9]([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)[C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1)[C:4]([O:6]CC)=[O:5])#[N:2].[OH-].[Li+].Cl>O1CCCC1.O>[C:1]([C:3](=[C:9]([C:10]1[CH:11]=[CH:12][C:13]([F:16])=[CH:14][CH:15]=1)[C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)[C:4]([OH:6])=[O:5])#[N:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 14539520HCID 14539520, compound

Product 1

HCID 14890664HCID 14890664, compoundYield 67.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-cyano-3,3-bis(4-fluorophenyl)-2-propenoate (5.0 g, 16 mmol) in tetrahydrofuran (30 mL) at 0° C. was added a solution of 1 M lithium hydroxide in water (30 ML). Saponification reaction was allowed to proceed at 0° C. for a total of three hours forming a clear homogeneous solution. Crude reaction mixture was made acidic by adding 15 mL of 3 M HCl solution in water and the organic material was extracted twice into diethyl ether. Organic layers were combined, dried over MgSO4 and concentrated under reduced pressure to give a pale solid. Recrystallization from ethyl acetate-hexanes mixture (1:9 v/v) yielded 3.08 g of the title compound; m.p.=180°-181° C. Another 1.37 g of the desired product was also isolated from the mother liquor making the total combined yield of the title compound over 97%.

Workup

  1. customSaponification reaction
  2. customto proceed at 0° C. for a total of three hours
  3. customforming a clear homogeneous solution
  4. customCrude reaction mixture
  5. extractionthe organic material was extracted twice into diethyl ether
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customto give a pale solid
  9. customRecrystallization from ethyl acetate-hexanes mixture (1:9 v/v)

Sources & evidence

ORD record
ord-e14094a4f7484e16b389fc3f41e7515b
Source dataset
uspto-grants-1991_07
Patent number
US05028730

Reaction notes

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