Water → HCID 23112892, compound

HRID 1170849Notes

Reaction equation

HRID 1170849 reaction equation
CC(C[AlH]CC(C)C)C.C1(C)C=CC=CC=1.[Cl:17][C:18]1[CH:19]=[C:20]([N:25]2[C:33]3[CH2:32][CH2:31][CH2:30][CH:29]([CH2:34][C:35](OCC)=[O:36])[C:28]=3[CH:27]=[N:26]2)[CH:21]=[CH:22][C:23]=1[Cl:24].O>C(Cl)Cl>[Cl:17][C:18]1[CH:19]=[C:20]([N:25]2[C:33]3[CH2:32][CH2:31][CH2:30][CH:29]([CH2:34][CH2:35][OH:36])[C:28]=3[CH:27]=[N:26]2)[CH:21]=[CH:22][C:23]=1[Cl:24]

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 14487Diisobutylaluminum hydrideHCID 23112893HCID 23112893, compound

Product 1

HCID 23112892HCID 23112892, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-65 °C

Procedure

A solution of DIBALH (1 M) in toluene (13 mL, 13.0 mmol) is slowly added, maintaining the reaction temperature under −65° C., to a solution of ethyl 2-(1-(3,4-dichlorophenyl)-4,5,6,7-tetrahydro-1H-indazol-4-yl)acetate (1.83 g, 5.2 mmol) in 20 mL of dried Cl2CH2 cooled at −75° C. under N2 atmosphere. The resulting mixture is maintained under stirring at −70° C. during 30 minutes, effecting a follow-up of the reaction by TLC. Next, the temperature is raised to 0° C., and 10 mL of cold water are added, while the temperature is maintained at 0° C. A precipitate is formed, which is filtered and washed with Cl2CH2. The organic phase is washed twice with water, dried, and evaporated under reduced pressure. The resulting crude is purified by silica-gel chromatography, giving 2-(1-(3,4-dichlorophenyl)-4,5,6,7-tetrahydro-1H-indazol-4-yl)ethanol (1.06 g, 3.41 mmol, 66%, oil).

Workup

  1. temperatureThe resulting mixture is maintained
  2. customa follow-up of the reaction by TLC
  3. temperatureNext, the temperature is raised to 0° C.
  4. temperatureis maintained at 0° C
  5. customA precipitate is formed
  6. filtrationwhich is filtered
  7. washwashed with Cl2CH2
  8. washThe organic phase is washed twice with water
  9. customdried
  10. customevaporated under reduced pressure
  11. customThe resulting crude is purified by silica-gel chromatography

Sources & evidence

ORD record
ord-75d087ceea294f4092d448a9aa8d9efc
Source dataset
uspto-grants-2010_11
Patent number
US07829559B2

Reaction notes

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