Water → HCID 68934618, compound

HRID 875100Notes

Reaction equation

HRID 875100 reaction equation
[CH3:1][N:2]1[C:10]2[C:9](=[O:11])[CH2:8][C:7]([CH3:13])([CH3:12])[CH2:6][C:5]=2[C:4]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:3]1.[O-:19][CH2:20]C.[Na+].O>C(OCC)=O>[OH:19][CH:20]=[C:8]1[C:9](=[O:11])[C:10]2[N:2]([CH3:1])[N:3]=[C:4]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:5]=2[CH2:6][C:7]1([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 962WaterHCID 2723922Sodium ethoxideHCID 57531656HCID 57531656, compound

Product 1

HCID 68934618HCID 68934618, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 8025Ethyl formateSolvent

Procedure

A solution of ethyl 1,5,5-trimethyl-7-oxo-4,5,6,7-tetrahydro-1H-indazole-3-carboxylate (1.00 g, 4 mmol) in anhydrous ethyl formate (10 mL) was treated with sodium ethoxide (0.54 g, 8 mmol) and refluxed for 3 hours. The mixture was cooled to room temperature and poured into cold water (40 mL). The aqueous layer was washed with diethyl ether (40 mL) to remove unreacted starting material, acidified with a 20% NaH2PO4 solution and extracted with ethyl acetate (50 mL×2). The organic extracts were collected, dried on Na2SO4 and evaporated to dryness to obtain the title compound (0.88 g, 78.8% yield) as a brown solid.

Workup

  1. temperaturerefluxed for 3 hours
  2. washThe aqueous layer was washed with diethyl ether (40 mL)
  3. customto remove unreacted
  4. extractionextracted with ethyl acetate (50 mL×2)
  5. customThe organic extracts were collected
  6. customdried on Na2SO4
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-df978f425368411f8804f7a99a76a76d
Source dataset
uspto-grants-2015_03
Patent number
US08981089B2

Reaction notes

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