Acetic Acid → Methyl {[2-(2-Acetoxyethyl)-6,7-dichloro-2,3-dihydro-1-oxo-2-(3-oxobutyl)-1H-inden-5-yl]oxy}acetate

HRID 569301Notes

Reaction equation

HRID 569301 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH:7]1[CH2:15][C:14]2[C:9](=[C:10]([Cl:23])[C:11]([Cl:22])=[C:12]([O:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH:13]=2)[C:8]1=[O:24])(=[O:3])[CH3:2].N12CCCC1=CCCN2.[CH:34]([C:36]([CH3:38])=[O:37])=[CH2:35].C(O)(=O)C>O1CCCC1.N12CCCC1=CCCN2.C(OCC)(=O)C>[C:1]([O:4][CH2:5][CH2:6][C:7]1([CH2:35][CH2:34][C:36](=[O:37])[CH3:38])[CH2:15][C:14]2[C:9](=[C:10]([Cl:23])[C:11]([Cl:22])=[C:12]([O:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH:13]=2)[C:8]1=[O:24])(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 6570Methyl vinyl ketone2×HCID 14098156Methyl {[2-(2-Acetoxyethyl)-6,7-dichloro-2,3-dihydro-1-oxo-1H-inden-5-yl]oxy}acetateHCID 21585024Diazabicyclo[4.3.0]non-5-ene

Product 1

HCID 14098157Methyl {[2-(2-Acetoxyethyl)-6,7-dichloro-2,3-dihydro-1-oxo-2-(3-oxobutyl)-1H-inden-5-yl]oxy}acetate

Reagents, catalysts & solvents 3

HCID 21585024Diazabicyclo[4.3.0]non-5-eneCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

Methyl {[2-(2-acetoxyethyl)-6,7-dichloro-2,3-dihydro-1-oxo-1H-inden-5-yl]oxy}acetate (3.2 gm, 0.00853 mole) was dissolved in tetrahydrofuran (30 ml), stirred and heated to 40° C. Then diazabicyclo[4.3.0]non-5-ene (50 microliters) was added followed by methyl vinyl ketone (1.2 gm, 0.0170 mole). The mixture was stirred and heated at 50°-52° C. for 100 minutes, then more diazabicyclo[4.3.0]non-5-ene (2 drops) and methyl vinyl ketone (0.6 ml) were added and stirring and heating continued for another 140 minutes. The mixture was cooled, diluted with ethyl acetate, poured into ice water (250 ml) containing acetic acid (1 ml). The layers were separated and the aqueous layer extracted first with methylene chloride then with ether. The combined organic extracts were washed with water and dried over MgSO4. Evaporation of the solvents in vacuo gave the product (3.6 gm.).

Workup

  1. stirringThe mixture was stirred
  2. temperatureheated at 50°-52° C. for 100 minutes
  3. stirringstirring
  4. temperatureheating
  5. temperatureThe mixture was cooled
  6. customThe layers were separated
  7. extractionthe aqueous layer extracted first with methylene chloride
  8. washThe combined organic extracts were washed with water
  9. dry with materialdried over MgSO4
  10. customEvaporation of the solvents in vacuo
  11. customgave the product (3.6 gm.)

Sources & evidence

ORD record
ord-3e94d8b44e6249bdb54f9e666a996e9a
Source dataset
uspto-grants-1988_03
Patent number
US04731471

Reaction notes

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