Diethyl Malonate → 5-(2,3-Dihydro-2,2,4,5,6-pentamethylbenzofuran-7-yl)cyclohexane-1,3-dione

HRID 1780610Notes

Reaction equation

HRID 1780610 reaction equation
[Na].C(OCC)(=O)[CH2:3][C:4](OCC)=[O:5].[CH3:13][C:14]1([CH3:31])[CH2:18][C:17]2[C:19]([CH3:30])=[C:20]([CH3:29])[C:21]([CH3:28])=[C:22]([CH:23]=[CH:24][C:25](=[O:27])[CH3:26])[C:16]=2[O:15]1.[OH-].[Na+]>CO>[CH3:13][C:14]1([CH3:31])[CH2:18][C:17]2[C:19]([CH3:30])=[C:20]([CH3:29])[C:21]([CH3:28])=[C:22]([CH:23]3[CH2:3][C:4](=[O:5])[CH2:26][C:25](=[O:27])[CH2:24]3)[C:16]=2[O:15]1

Participants

6

Reactant 4

HCID 7761Diethyl MalonateHCID 14798Sodium HydroxideHCID 5360545SodiumHCID 540298864-(2,3-Dihydro-2,2,4,5,6-pentamethylbenzofuran-7-yl)-3-buten-2-one

Product 1

HCID 190470655-(2,3-Dihydro-2,2,4,5,6-pentamethylbenzofuran-7-yl)cyclohexane-1,3-dione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 1.57 g of sodium in 68 ml of absolute methanol was added 10.35 ml of diethyl malonate. After stirring for 20 minutes, the mixture was added 8 g of the 4-(2,3-dihydro-2,2,4,5,6-pentamethylbenzofuran-7-yl)-3-buten-2-one in 17.5 g of absolute methanol, refluxed for 4 hours and added 150 g of 5% aqueous solution of sodium hydroxide. The reaction mixture was cooled to room temperature and washed three times with 50 ml of diethyl ether. 2N aqueous solution of hydrochloric acid was added dropwise into the aqueous layer until the bubble of carbon dioxide ceased. And then, solid was dissolved in ethyl acetate and washed with water. The combined organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford 16.7 g of 5-(2,3-dihydro-2,2,4,5,6-pentamethyl-benzofuran-7-yl)cyclohexane-1,3-dione as a yellow solid.

Workup

  1. temperaturerefluxed for 4 hours
  2. washwashed three times with 50 ml of diethyl ether
  3. addition2N aqueous solution of hydrochloric acid was added dropwise into the aqueous layer until the
  4. custombubble of carbon dioxide
  5. dissolutionAnd then, solid was dissolved in ethyl acetate
  6. washwashed with water
  7. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7104c40dfa8e4c1896a93babc680ed9e
Source dataset
uspto-grants-1997_05
Patent number
US05631208

Reaction notes

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