Potassium Carbonate → HCID 19822278, compound

HRID 1030381Notes

Reaction equation

HRID 1030381 reaction equation
Br[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[C:10]([O:13][C:14]1[C:15]([CH3:43])=[C:16]2[C:21](=[C:22]([CH3:25])[C:23]=1[CH3:24])[O:20][C:19]([CH2:27][O:28][C:29]1[CH:42]=[CH:41][C:32]([CH2:33][CH:34]3[S:38][C:37](=[O:39])[NH:36][C:35]3=[O:40])=[CH:31][CH:30]=1)([CH3:26])[CH2:18][CH2:17]2)(=[O:12])[CH3:11].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:10]([O:13][C:14]1[C:15]([CH3:43])=[C:16]2[C:21](=[C:22]([CH3:25])[C:23]=1[CH3:24])[O:20][C:19]([CH2:27][O:28][C:29]1[CH:42]=[CH:41][C:32]([CH2:33][CH:34]3[S:38][C:37](=[O:39])[N:36]([CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])[C:35]3=[O:40])=[CH:31][CH:30]=1)([CH3:26])[CH2:18][CH2:17]2)(=[O:12])[CH3:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 9869915HCID 9869915, compound

Product 1

HCID 19822278HCID 19822278, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

0.87 g of t-butyl bromoacetate was added dropwise, whilst ice-cooling, to a mixture of 1 g of 5-[4-(6-acetoxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl ]thiazolidine-2,4-dione [prepared as described in Example 3(b) of copending U.S. Ser. No. 644,996], 0.43 g of anhydrous potassium carbonate, and 8 ml of acetone. The resulting mixture was stirred for 2 hours at room temperature and then allowed to stand for 2 days, also at room temperature. The reaction mixture was then poured into ice-water and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off and the residue was subjected to silica gel column chromatography (eluent:benzene) to give the title compound.

Workup

  1. customprepared
  2. waitto stand for 2 days, also at room temperature
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-5ce0c162a8f44bc5b622d3d81707d93d
Source dataset
uspto-grants-1992_04
Patent number
US05104888

Reaction notes

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