p-Toluenesulfonic acid → HCID 14153439, compound

HRID 2371365Notes

Reaction equation

HRID 2371365 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH:12]([O:17][CH3:18])([O:15][CH3:16])OC.[CH2:19]([O:21][C:22]([CH:24]1[C:31](=[O:32])[CH:30]([C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH:29]2[CH:25]1[CH2:26]C(=O)[CH2:28]2)=[O:23])[CH3:20].C(=O)(O)[O-].[Na+]>CO>[CH2:36]([O:35][C:33]([CH:30]1[C:31](=[O:32])[CH:24]([C:22]([O:21][CH2:19][CH3:20])=[O:23])[CH:25]2[CH:29]1[CH2:28][C:12]([O:15][CH3:16])([O:17][CH3:18])[CH2:26]2)=[O:34])[CH3:37]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 516892Sodium BicarbonateHCID 12914184Diethyl 2,5-dioxooctahydropentalene-1,3-dicarboxylate

Product 1

HCID 14153439HCID 14153439, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

At 25° C., 330 mg of p-toluenesulfonic acid and 1.6 ml of trimethyl orthoformate are added to a solution of 9.6 g of 2,4-bisethoxycarbonylbicyclo[3.3.0]octane-3,7-dione (preparation: Reference Example 1) in 330 ml of methanol. The mixture is stirred for 3 hours at 25° C., combined with 80 ml of 5% strength sodium bicarbonate solution, extracted three times with respectively 300 ml of methylene chloride, dried over sodium sulfate, and evaporated under vacuum. The residue is purified by chromatography on silica gel. With ethyl acetate/hexane (1+1), 7 g of the title compound is obtained as a colorless oil.

Workup

  1. extractionextracted three times with respectively 300 ml of methylene chloride
  2. dry with materialdried over sodium sulfate
  3. customevaporated under vacuum
  4. customThe residue is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-db9db378eacf4571b0563b8385cb04d9
Source dataset
uspto-grants-1992_03
Patent number
US05093250

Reaction notes

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