Potassium Carbonate → HCID 22143531, compound

HRID 985198Notes

Reaction equation

HRID 985198 reaction equation
[C:1](OC1C=CC2C=C(C)SC=2C=1)(=[O:3])C.C(Cl)(=O)C(Cl)=O.[Al+3].[Cl-].[Cl-].[Cl-].C[O:26][C:27]1[CH:28]=[CH:29][C:30]2[C:34]([C:35](Cl)=[O:36])=[C:33]([CH3:38])[S:32][C:31]=2[CH:39]=1.C([O-])([O-])=O.[K+].[K+]>CO>[OH:26][C:27]1[CH:28]=[CH:29][C:30]2[C:34]([C:35]([O:3][CH3:1])=[O:36])=[C:33]([CH3:38])[S:32][C:31]=2[CH:39]=1

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 22143532HCID 22143532, compoundHCID 22143646HCID 22143646, compound

Product 1

HCID 22143531HCID 22143531, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

This material was prepared from 6-acetoxy-2-methylbenzo[b]thiophene 8b (500 mg, 2.42 mmole) by acylation with oxalyl chloride in the presence of AlCl3 as previously described for example 1c. A solution of the crude 6-methoxy-2-methylbenzo[b]thiophene-3-carbonyl chloride in MeOH (24 ml) was cooled to 0° C. prior to the addition of K2CO3 (351 mg, 2.66 mmole). The reaction was warmed to ambient temperature and stirred 3 hours. The solvent was removed, in vacuo, and the resulting residue was diluted with CH2Cl2 (75 ml) and H2O (25 ml). The organic layer was separated and the aqueous layer was extracted with CH2Cl2 (50 ml). The combined organics were washed with brine (25 ml), dried (Na2SO4), filtered, and concentrated in vacuo to afford the 468 mg (87%) of a pale brown solid. 1H NMR (300 MHz, DMSO-d6) δ9.68 (1H, s), 8.06 (1H, d, J=8.9 Hz), 7.23 (1H, d, J=2.3 Hz), 6.91 (1H, dd, J=2.3, 8.9 Hz).

Workup

  1. customThe solvent was removed, in vacuo
  2. additionthe resulting residue was diluted with CH2Cl2 (75 ml) and H2O (25 ml)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with CH2Cl2 (50 ml)
  5. washThe combined organics were washed with brine (25 ml)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9e73009af89348b1a9ad4c9c4f4e3e96
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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