Water → HCID 19047067, compound

HRID 1780605Notes

Reaction equation

HRID 1780605 reaction equation
[Na].C(OCC)(=O)[CH2:3][C:4](OCC)=[O:5].[Cl:13][C:14]1[C:22]2[O:21][C:20]([CH3:24])([CH3:23])[CH2:19][C:18]=2[C:17]([CH3:25])=[C:16]([CH3:26])[C:15]=1[CH:27]=[CH:28][C:29](=[O:31])[CH3:30].O>CO>[Cl:13][C:14]1[C:22]2[O:21][C:20]([CH3:23])([CH3:24])[CH2:19][C:18]=2[C:17]([CH3:25])=[C:16]([CH3:26])[C:15]=1[CH:27]1[CH2:3][C:4](=[O:5])[CH:30]=[C:29]([OH:31])[CH2:28]1

Participants

6

Reactant 4

HCID 962WaterHCID 7761Diethyl MalonateHCID 5360545SodiumHCID 54357790HCID 54357790, compound

Product 1

HCID 19047067HCID 19047067, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 1.0 g of sodium in 30 ml of absolute methanol was added 6.5 ml of diethyl malonate and 10 g of the 4-(7-chloro-2,3-dihydro-2,2,4,5-tetramethyl-benzofuran-6-yl)-3-buten-2-one in 20 ml of absolute methanol, and refluxed for 4 hours. The reaction mixture was added 100 ml of water and concentrated under reduced pressure and then added 17 g of 20% aqueous solution of sodium hydroxide. After refluxing 1 hour, the reaction mixture was cooled to room temperature and washed with benzene. Concentrated 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 11.8 g of 5-(7-chloro-2,3-dihydro-2,2,4,5-tetramethylbenzofuran-6-yl)-3-hydroxycyclohex-2-en-1-one.

Workup

  1. temperaturerefluxed for 4 hours
  2. concentrationconcentrated under reduced pressure
  3. additionadded 17 g of 20% aqueous solution of sodium hydroxide
  4. temperatureAfter refluxing 1 hour
  5. washwashed with benzene
  6. additionConcentrated hydrochloric acid was added dropwise into the aqueous layer until the
  7. custombubble of carbon dioxide
  8. dissolutionAnd then, solid was dissolved in ethyl acetate
  9. washwashed with water
  10. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f0a191568d2f4f29928472a07ddfc04c
Source dataset
uspto-grants-1997_05
Patent number
US05631208

Reaction notes

Loading…