Diethyl Malonate → HCID 19047063, compound

HRID 1780617Notes

Reaction equation

HRID 1780617 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]([CH:24]=[CH:25][C:26](=[O:28])[CH3:27])=[C:22]([CH3:23])[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]([CH:24]3[CH2:3][C:4](=[O:5])[CH:27]=[C:26]([OH:28])[CH2:25]3)=[C:22]([CH3:23])[C:16]=2[O:15]1

Participants

6

Reactant 4

HCID 7761Diethyl MalonateHCID 14798Sodium HydroxideHCID 5360545SodiumHCID 53953563HCID 53953563, compound

Product 1

HCID 19047063HCID 19047063, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 3.8 g of sodium 140 ml of absolute methanol was added 25 ml of diethyl malonate. After stirring for 20 minutes, the mixture was added 42.4 g of the 4-(2,3-dihydro-2,2,4,5,7-pentamethylbenzofuran-6-yl)-3-butene-2-one in 140 ml of absolute methanol, refluxed for 4 hours and 200 ml of 10% aqueous solution of sodium hydroxide. The reaction mixture was cooled to room temperature and washed with diethyl ether. 2N aqueous solution of hydrochloric acid was added dropwise into the aqueous layer until the bubble 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 38.8 g of 5-(2,3-dihydro-2,2,4,5,7-pentamethylbenzofuran-6-yl)-3-hydroxycyclohex-2-en-1-one.

Workup

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

Sources & evidence

ORD record
ord-0f6b925a073f4d578acac7b182c2c722
Source dataset
uspto-grants-1997_05
Patent number
US05631208

Reaction notes

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