Methyl vinyl ketone → HCID 53671021, compound

HRID 2291540Notes

Reaction equation

HRID 2291540 reaction equation
[Cl:1][C:2]1[C:10]([Cl:11])=[C:9]2[C:5]([CH:6]([CH3:15])[CH:7]([CH2:13][CH3:14])[C:8]2=[O:12])=[CH:4][C:3]=1[O:16][CH2:17][C:18]([O:20][CH3:21])=[O:19].C([C:24]([CH3:26])=[O:25])=C.N12CCCC1=NC[CH2:29][CH2:28]2>O1CCCC1>[Cl:1][C:2]1[C:10]([Cl:11])=[C:9]2[C:5]([CH:6]([CH3:15])[C:7]([CH2:28][CH3:29])([CH2:13][CH2:14][C:24](=[O:25])[CH3:26])[C:8]2=[O:12])=[CH:4][C:3]=1[O:16][CH2:17][C:18]([O:20][CH3:21])=[O:19]

Participants

5

Reactant 3

HCID 6570Methyl vinyl ketoneHCID 763491,5-Diazabicyclo(4.3.0)non-5-ene2×HCID 53840282HCID 53840282, compound

Product 1

HCID 53671021HCID 53671021, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl [(6,7-dichloro-2-ethyl-2,3-dihydro-3-methyl-1-oxo-1H-inden-5-yl)oxy]acetate (0.8 g) in tetrahydrofuran (7.5 ml) was added methyl vinyl ketone (0.45 ml) and 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) (75 μl). The reaction mixture was heated at 60° C. for five hours during which time DBN (2×75 μl) was added. The reaction mixture was poured into ice water, extracted with ether, washed with water, dried over MgSO4 and evaporated in vacuo. Chromatography on silica gel eluting with ethyl acetate-hexane (1:1) gave methyl [(6,7-dichloro-2-ethyl-2,3-dihydro-3-methyl-1-oxo-2-(3-oxobutyl)-1H-inden-5-yl)oxy]acetate which was used in Step B without further purification.

Workup

  1. additionwas added
  2. extractionextracted with ether
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-7670e90e16634072b8aa6f340566d1e6
Source dataset
uspto-grants-1989_01
Patent number
US04797391

Reaction notes

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