5-chloro-1,3-diphenyl-1H-pyrazole-4-carbaldehyde → (5-Chloro-1,3-diphenyl-1H-pyrazol-4-YL)-methanol

HRID 1283204Notes

Reaction equation

HRID 1283204 reaction equation
[Cl:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:3]=1[CH:19]=[O:20].[BH4-].[Na+].ClC1N(C2C=CC=CC=2)N=C(C2C=CC=CC=2)C=1CO.O>O1CCOCC1.O>[Cl:1][C:2]1[N:6]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:5]=[C:4]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:3]=1[CH2:19][OH:20]

Participants

6

Reactant 3

HCID 7366595-chloro-1,3-diphenyl-1H-pyrazole-4-carbaldehydeHCID 4311764Sodium borohydrideHCID 86733818Water 5-chloro-4-hydroxymethyl-1,3-diphenyl-pyrazole

Product 1

HCID 4913351(5-Chloro-1,3-diphenyl-1H-pyrazol-4-YL)-methanolYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 21 g of 5-chloro-1,3-diphenyl-pyrazole-4-carboxaldehyde in 80 ml of dioxan there is added dropwise at 23° to 27° a solution of 1.11 g of sodium borohydride in 35 ml of water. The resulting suspension is stirred for a further 30 minutes and on the addition of 200 ml of water 5-chloro-4-hydroxymethyl-1,3-diphenyl-pyrazole is precipitated with a 99% yield; F 140.5°-141.5° (from toluene).

Workup

  1. customis precipitated with a 99% yield
  2. customF 140.5°-141.5° (from toluene)

Sources & evidence

ORD record
ord-4d78435d51824562963bc403d73b23e6
Source dataset
uspto-grants-1976_08
Patent number
US03974176

Reaction notes

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