Water → HCID 21507689, compound

HRID 1287310Notes

Reaction equation

HRID 1287310 reaction equation
[CH2:1]([N:8]1[C:12]([C:13](OCC)=[O:14])=[C:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:10]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C(OCC)C>[CH2:1]([N:8]1[C:12]([CH2:13][OH:14])=[C:11]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:10]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 21226445Aluminium lithium hydrideHCID 21507693HCID 21507693, compound

Product 1

HCID 21507689HCID 21507689, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

228 Grams of crude ethyl 1-benzyl-3,4-diphenylpyrazole-5-carboxylate (prepared as described below) dissolved in 3200 ml of anhydrous diethyl ether are added, at 0°C and under a nitrogen atmosphere, to 47 grams of lithium aluminium hydride suspended in 1600 ml of anhydrous diethyl ether. The solution is stirred overnight at ambient temperature and then cooled to 0° C, whereupon 55 ml of water, 20.2 ml of 10N soda and 83 ml of water are slowly and successively added under a nitrogen atmosphere, and the resulting precipitate is filtered. The filtrate is evaporated under reduced pressure and the residue is dissolved in 360 ml of di-isopropyl ether. 1 -Benzyl-3,4-diphenyl-5-hydroxymethylpyrazole melting at 138° C is thus obtained.

Workup

  1. additionsuccessively added under a nitrogen atmosphere
  2. filtrationthe resulting precipitate is filtered
  3. customThe filtrate is evaporated under reduced pressure
  4. dissolutionthe residue is dissolved in 360 ml of di-isopropyl ether

Sources & evidence

ORD record
ord-5076815f4ada4a4694ce808dfe6923c0
Source dataset
uspto-grants-1976_10
Patent number
US03984431

Reaction notes

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