HCID 178469914, compound → HCID 178519878, compound

HRID 436902Notes

Reaction equation

HRID 436902 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13](OCC)=[O:14])=[CH:11][NH:10][N:9]=2)=[CH:4][CH:3]=1>O1CCCC1.C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([CH2:13][OH:14])=[CH:11][NH:10][N:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 178469914HCID 178469914, compound

Product 1

HCID 178519878HCID 178519878, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 12 g of ethyl-(4-chloro-phenyl-4-ethoxycarbonyl-pyrazole in 150 ml of tetrahydrofuran is cooled in an ice bath. Then 25 ml of a 1 molar solution of aluminum hydride triethylamine complex in benzene is added dropwise. After the addition, the ice bath is removed and the gelatinous mixture stirred at room temperature for 21/2 hours. Excess reagent is then destroyed by the dropwise addition of water followed by 30 ml of an aqueous 2N solution of sodium hydroxide. The layers are separated, the aqueous phase reextracted with ethyl acetate and the combined organic layers dried over anhydrous sodium sulfate. The recrystallization of the solid residue from hot ethyl acetate gives the 3-(4-chloro-phenyl)-4-hydroxymethyl-pyrazole, m.p. 149°-150°.

Workup

  1. additionAfter the addition
  2. customthe ice bath is removed
  3. customExcess reagent is then destroyed by the dropwise addition of water
  4. customThe layers are separated
  5. dry with materialthe combined organic layers dried over anhydrous sodium sulfate
  6. customThe recrystallization of the solid residue from hot ethyl acetate

Sources & evidence

ORD record
ord-596db95e7d204302a02a3a31a9678c64
Source dataset
uspto-grants-1977_06
Patent number
US04028381

Reaction notes

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