Potassium Carbonate → HCID 54440903, compound

HRID 326301Notes

Reaction equation

HRID 326301 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]([OH:18])[CH:3]=1)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3.Br[CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].C(=O)([O-])[O-].[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]=[C:4]([O:18][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:3]=1)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 15149208HCID 15149208, compound

Product 1

HCID 54440903HCID 54440903, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

According to the same procedure as in Preparation 46, 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 4-bromobutyrate (0.215 g, 1.1 mmol), anhydrous potassium carbonate (0.207 g, 1.5 mmol), and acetonitrile (3 ml) is reacted and treated. The resulting extract is concentrated and the residue is purified by a silica gel column chromatography (eluent: acetone and dichlomethane, 1:50) to obtain the title compound as an oil (0.236 g, yield 64.9%).

Workup

  1. customAccording to the same procedure as in Preparation 46
  2. customis reacted
  3. additiontreated
  4. extractionThe resulting extract
  5. concentrationis concentrated
  6. customthe residue is purified by a silica gel column chromatography (eluent: acetone and dichlomethane, 1:50)

Sources & evidence

ORD record
ord-3715a9ca03db489abfc7a1de6af61fbf
Source dataset
uspto-grants-1993_12
Patent number
US05268386

Reaction notes

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