Chloroacetone → HCID 12257245, compound

HRID 1729706Notes

Reaction equation

HRID 1729706 reaction equation
[OH:1][C:2]1[C:3]2[CH:14]=[CH:13][CH:12]=[CH:11][C:4]=2[S:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8].[CH3:15][C:16](C)([O-:18])[CH3:17].[K+].ClCC(=O)C>CS(C)=O>[C:16]([CH2:17][O:1][C:2]1[C:3]2[CH:14]=[CH:13][CH:12]=[CH:11][C:4]=2[S:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8])(=[O:18])[CH3:15]

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 83165Methyl 3-hydroxybenzo(b)thiophene-3-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 12257245HCID 12257245, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 12.6 g. of the product of Example 1 and 8.1 g. of potassium t-butoxide in 100 ml. of dimethyl sulfoxide was added, dropwise with stirring, 15 ml. of chloroacetone. The mixture was treated and the product was recovered as shown in Example 2, except that the product was crystallized from ethanol-water. The product was 10.7 g. of 3-(acetlymethoxy)benzo[b]thiophene-2-carboxylic acid, methyl ester, m.p. 57°-58°C. It was identified by NMR analysis and elemental microanalysis as follows.

Workup

  1. additionThe mixture was treated
  2. customthe product was recovered
  3. customwas crystallized from ethanol-water

Sources & evidence

ORD record
ord-9211576c723a4c279550860f18329291
Source dataset
uspto-grants-1976_11
Patent number
US03989718

Reaction notes

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