Hydrochloric Acid → HCID 67442988, compound

HRID 1667649Notes

Reaction equation

HRID 1667649 reaction equation
[OH-].[Li+].[C:3]([CH2:5]P(=O)(OCC)OCC)#[N:4].[C:14]([C:18]1[CH:44]=[CH:43][C:21]([CH2:22][O:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]3[CH:35]=[CH:34][C:33]([O:36][C:37]([F:40])([F:39])[F:38])=[CH:32][CH:31]=3)=[CH:26][C:25]=2[CH:41]=O)=[CH:20][CH:19]=1)([CH3:17])([CH3:16])[CH3:15].Cl>O1CCCC1>[C:14]([C:18]1[CH:44]=[CH:43][C:21]([CH2:22][O:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]3[CH:31]=[CH:32][C:33]([O:36][C:37]([F:39])([F:40])[F:38])=[CH:34][CH:35]=3)=[CH:26][C:25]=2[CH:41]=[CH:5][C:3]#[N:4])=[CH:20][CH:19]=1)([CH3:16])([CH3:17])[CH3:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 58007939HCID 58007939, compound

Product 1

HCID 67442988HCID 67442988, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of lithium hydroxide (101 mg, 2.40 mmol), diethyl cyanomethylphosphonate (390 mg, 2.20 mmol) and tetrahydrofuran (20 ml) was stirred at 70° C. for 30 minutes under argon atmosphere. After the reaction mixture was cooled to room temperature, 4-[4-(tert-butyl)benzyloxy]-4′-(trifluoromethoxy)biphenyl-3-carbaldehyde (compound of Example 4 (2); 857 mg, 2.00 mmol) was added, and the mixture was stirred at room temperature for 4 hours. 1N Hydrochloric acid was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel (n-hexane:ethyl acetate=10:1) to give the title compound (631 mg, 70.0%) as a colorless oil.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. stirringthe mixture was stirred at room temperature for 4 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe residue obtained by evaporation of the solvent under reduced pressure
  7. customwas purified by column chromatography on silica gel (n-hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-b8b4788c684341afa39f3fb0170866fb
Source dataset
uspto-grants-2011_10
Patent number
US08044236B2

Reaction notes

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