Water → HCID 86721489, compound

HRID 869622Notes

Reaction equation

HRID 869622 reaction equation
[CH:1]1([C:4](=[C:7]2[C:13]3[CH:14]=[CH:15][C:16]([C:18]#[C:19][Si](C)(C)C)=[CH:17][C:12]=3[CH2:11][O:10][C:9]3[CH:24]=[C:25]([F:28])[CH:26]=[CH:27][C:8]2=3)[C:5]#[N:6])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].O>CO>[CH:1]1([C:4](=[C:7]2[C:13]3[CH:14]=[CH:15][C:16]([C:18]#[CH:19])=[CH:17][C:12]=3[CH2:11][O:10][C:9]3[CH:24]=[C:25]([F:28])[CH:26]=[CH:27][C:8]2=3)[C:5]#[N:6])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 86721490HCID 86721490, compound

Product 1

HCID 86721489HCID 86721489, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

[step 2] 2-Cyclopropyl-2-{3-fluoro-8-[(trimethylsilyl)ethynyl]dibenzo[b,e]oxepin-11(6H)-ylidene}acetonitrile (1.0 g, 2.6 mmol) obtained in step 1 was dissolved in methanol (10 mL), potassium carbonate (0.35 g, 2.6 mmol) was added, and the mixture was stirred at room temperature for 1 hr. The reaction was discontinued with water, and the mixture was extracted 3 times with ethyl acetate. The combined organic layers were washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was crystallized from isopropyl ether and collected by filtration to give the title compound (600 mg, 74%, E/Z=1/1).

Workup

  1. extractionthe mixture was extracted 3 times with ethyl acetate
  2. washThe combined organic layers were washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was crystallized from isopropyl ether
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-b68bb19c2bed4a958933cc61f2a0d5c7
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Reaction notes

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