Methanol → HCID 118468189, compound

HRID 629375Notes

Reaction equation

HRID 629375 reaction equation
[C:1]([C:3]1[C:12]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH:24]=[CH:23][CH:22]=[N:21]3)=[CH:16][CH:15]=2)=[CH:11][C:6]([C:7]([O:9]C)=[O:8])=[C:5]([CH:25]=[CH2:26])[C:4]=1[CH3:27])#[N:2].O.[OH-].[Li+].CO>C1COCC1.O>[C:1]([C:3]1[C:12]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([N:20]3[CH:24]=[CH:23][CH:22]=[N:21]3)=[CH:18][CH:19]=2)=[CH:11][C:6]([C:7]([OH:9])=[O:8])=[C:5]([CH:25]=[CH2:26])[C:4]=1[CH3:27])#[N:2]

Participants

6

Reactant 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 118468374HCID 118468374, compound

Product 1

HCID 118468189HCID 118468189, compoundYield 89.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
10 °C

Procedure

To a solution of methyl 4-cyano-2-ethenyl-3-methyl-5-[4-(1H-pyrazol-1-yl)benzyl]benzoate (0.70 g) in THF (5.00 mL)-water (5.00 mL) were added lithium hydroxide monohydrate (0.25 g) and methanol (1.00 mL), and the mixture was stirred at 10° C. for 16 hr. The reaction mixture was diluted with water, and the mixture was extracted with tert-butyl methyl ether. The aqueous layer was acidified with 2N hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (0.60 g).

Workup

  1. extractionthe mixture was extracted with tert-butyl methyl ether
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-1f7d93f92ca243e894eac2b6a0b07a6f
Source dataset
uspto-grants-2016_04
Patent number
US09315458B2

Reaction notes

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