Ethyl Acetoacetate → HCID 20296681, compound

HRID 1389509Notes

Reaction equation

HRID 1389509 reaction equation
[CH3:1][CH:2]([N:4]1[CH:12]([OH:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]1=O)[CH3:3].C(OCC)(=O)[CH2:16][C:17]([CH3:19])=[O:18]>S(=O)(=O)(O)O>[CH3:3][CH:2]([N:4]1[CH:5]([CH2:16][C:17](=[O:18])[CH3:19])[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:12]1=[O:13])[CH3:1]

Participants

4

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 11629744HCID 11629744, compound

Product 1

HCID 20296681HCID 20296681, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 2-(1-methylethyl)-3-hydroxy-1,3-dihydro-2H-isoindol-1-one (6.1 g, described in Example 12) and ethyl acetoacetate (12.4 g) in conc. sulfuric acid (60 ml) is stirred at 40° C. for 24 hr and poured into ice. The solution is extracted with ethyl acetate and the organic extract is washed with 5% aqueous sodium bicarbonate and water, dried and evaporated. The residue is chromatographed on silica gel using hexane-ethyl acetate (2:3) and the eluates are evaporated to give 3.7 g of the title compound, nmr (DMSO-d6) δ 1.25 (d, 3H), 1.35 (d, 3H), 2.05 (s, 3H), 2.5-3.4 (m, 2H), 3.95 (m, 1H), 4.9 (m, 1H) and 7.4 (m, 4H).

Workup

  1. additionpoured into ice
  2. extractionThe solution is extracted with ethyl acetate
  3. extractionthe organic extract
  4. washis washed with 5% aqueous sodium bicarbonate and water
  5. customdried
  6. customevaporated
  7. customThe residue is chromatographed on silica gel
  8. customthe eluates are evaporated

Sources & evidence

ORD record
ord-147176fa2c3d4042be540066b49333b8
Source dataset
uspto-grants-1981_01
Patent number
US04244966

Reaction notes

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