Water → HCID 68934618, compound

HRID 44592Notes

Reaction equation

HRID 44592 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-6dcce04b4e824615b3a58ff6811cf1f2
Source dataset
uspto-grants-2013_09
Patent number
US08541429B2

Reaction notes

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