Potassium Carbonate → HCID 53636550, compound

HRID 326300Notes

Reaction equation

HRID 326300 reaction equation
[OH:1][C:2]1[C:7]2[C:8](=[O:17])[CH2:9][C:10]3([O:16][C:6]=2[CH:5]=[C:4](O)[CH:3]=1)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3.Br[CH:20]([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22].C(=O)([O-])[O-:28].[K+].[K+]>C(#N)C>[OH:1][C:2]1[C:7]2[C:8](=[O:17])[CH2:9][C:10]3([O:16][C:6]=2[CH:5]=[CH:4][C:3]=1[O:28][CH:20]([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionateHCID 15149208HCID 15149208, compound

Product 1

HCID 53636550HCID 53636550, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 5,7-dihydroxyspiro[2H-1-benzopyran-2,1'-cyclohexan]-4(3H)-one (prepared in Preparation 19) (0.248 g, 1.0 mmol), ethyl 2-bromopropionate (0.199 g, 1.1 mmol), anhydrous potassium carbonate (0.207 g, 1.5 mmol), and acetonitrile (3 ml) is stirred at room temperature for 22 hours, and the reaction mixture is concentrated. To the residue is added saturated brine and the mixture is extracted with dichloromethane. The organic layer is separated, dried, and concentrated. Purification by a silica gel column chromatography (eluent: dichloromethane) gives the title compound as an oil (0.284 g, yield 81.6%).

Workup

  1. concentrationthe reaction mixture is concentrated
  2. additionTo the residue is added saturated brine
  3. extractionthe mixture is extracted with dichloromethane
  4. customThe organic layer is separated
  5. customdried
  6. concentrationconcentrated
  7. customPurification by a silica gel column chromatography (eluent: dichloromethane)

Sources & evidence

ORD record
ord-fb87fdbb7df844d0b993172129b82e21
Source dataset
uspto-grants-1993_12
Patent number
US05268386

Reaction notes

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