Ethyl bromoacetate → HCID 19736718, compound

HRID 326314Notes

Reaction equation

HRID 326314 reaction equation
[OH:1][C:2]1[C:7]2[C:8](=[O:17])[CH2:9][C:10]3([S: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][C:21]([O:23][CH2:24][CH3:25])=[O:22].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([S:16][C:6]=2[CH:5]=[C:4]([O:18][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:3]=1)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 19736736HCID 19736736, compound

Product 1

HCID 19736718HCID 19736718, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 5,7-dihydroxy-spiro [2H-1-benzothiine-2,1'-cyclohexan]-4(3H)-one (prepared in Preparation 79) (0.47 g, 1.78 mmol ), ethyl bromoacetate (0.297 g, 1.78 mmol), anhydrous potassium carbonate (0.368 g, 2.67 mmol), and dry acetonitrile (5 ml) is stirred overnight at room temperature. The mixture is stirred at 35° C. for additional 5 hours. The reaction mixture is filtered to remove inorganic materials. The solvent is removed by distillation from the filtrate. The residue is placed on a silica gel column and eluted with a mixture of dichloromethane and ethyl acetate (9:1) to obtain ethyl 2-{(5-hydroxy-3,4-dihydro-4-oxospiro[2H-1-benzothiine-2,1'-cyclohexan]-7-yl)oxy}acetate as a crystalline solid (0.57 g, 91.5%). Recrystallization from diethyl ether gives a product having a melting point of 87°-88° C.

Workup

  1. stirringThe mixture is stirred at 35° C. for additional 5 hours
  2. filtrationThe reaction mixture is filtered
  3. customto remove inorganic materials
  4. customThe solvent is removed by distillation from the filtrate
  5. washeluted with a mixture of dichloromethane and ethyl acetate (9:1)

Sources & evidence

ORD record
ord-114af90529b74d81bbb12f34c0d8e15a
Source dataset
uspto-grants-1993_12
Patent number
US05268386

Reaction notes

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