Water → HCID 68934618, compound

HRID 1455095Notes

Reaction equation

HRID 1455095 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 staring 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-7e2bb89ecd654cdcb5b5188736ddac52
Source dataset
uspto-grants-2009_01
Patent number
US07482354B2

Reaction notes

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