Sodium Hydroxide → HCID 67296510, compound

HRID 1802541Notes

Reaction equation

HRID 1802541 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)=[CH:12][C:11]([C:22]3([OH:32])[CH2:31][CH2:30][C:25]4(OCC[O:26]4)[CH2:24][CH2:23]3)=[N:10]2)=[CH:5][CH:4]=1.[OH-].[Na+].C(=O)(O)[O-].[Na+]>O1CCCC1.Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[C:13]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)=[CH:12][C:11]([C:22]3([OH:32])[CH2:31][CH2:30][C:25](=[O:26])[CH2:24][CH2:23]3)=[N:10]2)=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 67296597HCID 67296597, compound

Product 1

HCID 67296510HCID 67296510, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 8-(1,5-bis(4-methoxyphenyl)-1H-pyrazol-3-yl)-1,4-dioxaspiro[4.5]decan-8-ol (Reference Example 32) (658 mg, 1.50 mmol) in tetrahydrofuran (3.75 mL), 6 M hydrochloric acid (7.5 mL) was added at 0° C., and the obtained solution was stirred at room temperature for 5 hours. The reaction solution was neutralized by pouring it into ice-cooled 10% aqueous sodium hydroxide solution. The resulting solution was basified by addition of saturated sodium bicarbonate solution, and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, n-hexane/ethyl acetate) to obtain the title compound (523 mg, 1.33 mmol, 89%) as an amorphous product.

Workup

  1. additionby pouring it into ice-
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography (silica gel, n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-3fdaea3b13e7495196d312cf54179910
Source dataset
uspto-grants-2013_01
Patent number
US08349874B2

Reaction notes

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