Water → HCID 178458818, compound

HRID 1710263Notes

Reaction equation

HRID 1710263 reaction equation
[OH:1][C:2]1[CH2:7][CH:6]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[CH2:13][CH2:12][CH2:11]3)[CH2:5][C:4](=[O:17])[CH:3]=1.O.[C:19](O)(=[O:22])[CH2:20][CH3:21]>C(OC(=O)CC)(=O)CC.FC(S(O)(=O)=O)(F)F>[OH:17][C:4]1[CH2:5][CH:6]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[CH2:13][CH2:12][CH2:11]3)[CH2:7][C:2](=[O:1])[C:3]=1[C:19](=[O:22])[CH2:20][CH3:21]

Participants

6

Reactant 3

HCID 962WaterHCID 1032Propionic AcidHCID 137335195-(2,3-Dihydro-1H-inden-5-yl)-3-hydroxycyclohex-2-en-1-one

Product 1

HCID 178458818HCID 178458818, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 62406Trifluoromethanesulfonic acidCatalystHCID 31263Propionic anhydrideSolvent

Conditions

Temperature
130 °C

Procedure

3-Hydroxy-5-(5-indanyl)cyclohex-2-en-1-one (4.0 g; 18 mmole) was dissolved in a mixture of propionic acid (4 ml) and propionic anhydride (4 ml) at 130° C. under nitrogen. To the resulting clear solution was added 8 drops of trifluoromethyl sulphonic acid and the mixture was allowed to stir at 130° C. under nitrogen for a further 11/2 hours. The mixture was poured into water (500 ml) and stirred until all the anhydride had reacted (approx 30 min). The resulting solid was filtered off, pressed dry at the pump and then dissolved in dichloromethane and purified by column chromatography over silica gel (eluant dichloromethane) to give 3-hydroxy-5-(5-indanyl)-2-propionylcyclohex-2-en-1-one (1.88 g; 37%), mp 98° C.

Workup

  1. customhad reacted (approx 30 min)
  2. filtrationThe resulting solid was filtered off
  3. custompressed dry at the pump
  4. dissolutiondissolved in dichloromethane
  5. custompurified by column chromatography over silica gel (eluant dichloromethane)

Sources & evidence

ORD record
ord-efc93a82cc5a4e0cbbe2a6d01b850f62
Source dataset
uspto-grants-1990_08
Patent number
US04952722

Reaction notes

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