Diethyl Malonate → 5-(2,3-Dihydro-1H-inden-5-yl)-3-hydroxycyclohex-2-en-1-one

HRID 1195456Notes

Reaction equation

HRID 1195456 reaction equation
C(OCC)(=O)[CH2:2][C:3](OCC)=[O:4].[Na].[CH2:13]1[C:21]2[C:16](=[CH:17][C:18]([CH:22]=[CH:23][C:24](=[O:26])[CH3:25])=[CH:19][CH:20]=2)[CH2:15][CH2:14]1.[OH-].[Na+]>C(O)C.O>[OH:26][C:24]1[CH2:23][CH:22]([C:18]2[CH:17]=[C:16]3[C:21](=[CH:20][CH:19]=2)[CH2:13][CH2:14][CH2:15]3)[CH2:2][C:3](=[O:4])[CH:25]=1

Participants

7

Reactant 4

HCID 7761Diethyl MalonateHCID 14798Sodium HydroxideHCID 40739273-Buten-2-one, 4-(2,3-dihydro-1H-inden-5-yl)-HCID 5360545Sodium

Product 1

HCID 137335195-(2,3-Dihydro-1H-inden-5-yl)-3-hydroxycyclohex-2-en-1-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

Diethyl malonate (17.5 g; 110 mmole) was added to a solution of sodium metal (1.91 g; 83 mmole) in anhydrous absolute ethanol (50 ml) and the mixture was heated to reflux temperature. A mixture of 1-(5-indanyl)but-1-en-3-one (19.25 g; 103 mmole) in anhydrous absolute ethanol (50 ml) was added over a period of two minutes and the mixture was heated under reflux for a period of 2 hours. An aqueous solution of sodium hydroxide (30% solution, 50 ml) was added and the mixture was heated under reflux for a further 11/2 hours. The solution was poured into water (200 ml) and the aqueous mixture was extracted twice with ethyl acetate (2×100 ml). The aqueous phase was acidified with concentrated hydrochloric acid and warmed gently until the evolution of carbon dioxide ceased. The aqueous mixture was extracted with ethyl acetate, dried over anhydrous sodium sulphate, and the solvent was removed by evaporation under reduced pressure using a rotary evaporator. The product, 3-hydroxy-5-(5-indanyl)cyclohex-2-en-1-one, was obtained as a white solid (18.70 g; 79.6%), mp 198° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux temperature
  3. additionwas added over a period of two minutes
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for a period of 2 hours
  6. temperaturethe mixture was heated
  7. temperatureunder reflux for a further 11/2 hours
  8. extractionthe aqueous mixture was extracted twice with ethyl acetate (2×100 ml)
  9. temperaturewarmed gently until the evolution of carbon dioxide
  10. extractionThe aqueous mixture was extracted with ethyl acetate
  11. dry with materialdried over anhydrous sodium sulphate
  12. customthe solvent was removed by evaporation under reduced pressure
  13. customa rotary evaporator

Sources & evidence

ORD record
ord-17d2f8d07228488eac1390f8317379a4
Source dataset
uspto-grants-1992_05
Patent number
US05110989

Reaction notes

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