Sodium Chloride → 1-(Indazol-1-yl)-3-(4-octylphenoxy)propan-2-ol

HRID 1821923Notes

Reaction equation

HRID 1821923 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[N:4]1.[CH2:12]([C:20]1[CH:30]=[CH:29][C:23]([O:24][CH2:25][CH:26]2[CH2:28][O:27]2)=[CH:22][CH:21]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[Na+].[Cl-]>CN(C=O)C>[N:3]1([CH2:28][CH:26]([OH:27])[CH2:25][O:24][C:23]2[CH:29]=[CH:30][C:20]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:21][CH:22]=2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[N:4]1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 92211H-IndazoleHCID 24758Sodium hydrideHCID 107248((p-Octylphenoxy)methyl)oxirane

Product 1

HCID 129928931-(Indazol-1-yl)-3-(4-octylphenoxy)propan-2-ol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

0.048 g (1.20 mmol) sodium hydride as a 60% dispersion in mineral oil is suspended in 10 ml absolute DMF, stirred at room temperature for 10 min and mixed with a solution of 0.135 g (1.14 mmol) indazole. Having stirred for 1 hour, a solution of 0.300 g (1.14 mmol) 2-(4-octylphenoxymethyl)oxirane in 10 ml absolute DMF is added drop-wise. The mixture is stirred for 40 hours, hydrolyzed with a semi-saturated NaCl solution and extracted four times using diethyl ether. The combined organic phases are concentrated to half the volume on the rotary evaporator and washed three times with saturated NaCl solution. Drying on sodium sulfate, filtration and reconcentration on the rotary evaporator leave a white solid which is recrystallized from petroleum ether/ethyl acetate (80:20).

Workup

  1. stirringHaving stirred for 1 hour
  2. extractionextracted four times
  3. concentrationThe combined organic phases are concentrated to half the volume
  4. customon the rotary evaporator
  5. washwashed three times with saturated NaCl solution
  6. customDrying on sodium sulfate, filtration and reconcentration on the rotary evaporator
  7. customleave a white solid which
  8. customis recrystallized from petroleum ether/ethyl acetate (80:20)

Sources & evidence

ORD record
ord-17c3f53e62c3400c89033b3c264f65ca
Source dataset
uspto-grants-2009_10
Patent number
US07608633B2

Reaction notes

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