Hydrochloric Acid → HCID 13961712, compound

HRID 2226877Notes

Reaction equation

HRID 2226877 reaction equation
[CH3:1][C:2](C)([O-])[CH3:3].[K+].[OH:7][C:8]1[C:12]2[CH:13]=[C:14]([O:17][CH3:18])[CH:15]=[CH:16][C:11]=2[O:10][C:9]=1[C:19]([O:21][CH3:22])=[O:20].BrC(C)C.Cl>CS(C)=O.O>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]2[O:10][C:9]([C:19]([O:21][CH3:22])=[O:20])=[C:8]([O:7][CH:2]([CH3:3])[CH3:1])[C:12]=2[CH:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 63582-BromopropaneHCID 23665647Potassium tert-butoxideHCID 54732577Methyl 3-hydroxy-5-methoxy-1-benzofuran-2-carboxylate

Product 1

HCID 13961712HCID 13961712, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

A solution of potassium tert-butoxide (12.0 g, 107 mmol) in 50 mL of methyl sulfoxide is cooled in a cold water bath while a solution of methyl 3-hydroxy-5-methoxy-2-benzofurancarboxylate (16.2 g, 73 mmol) [Connor D. T., et al., J. Med, Chem. 35, 958 (1992)] in 150 mL of methyl sulfoxide is added dropwise. The mixture is stirred for 45 minutes and 2-bromopropane (12.0 mL, 15.7 g, 128 mmol) is added in one portion. After stirring at room temperature for 48 hours, the mixture is added to 1.2 kg of ice and water and acidified with 6.0N HCl . The mixture is extracted with dichloromethane, and the combined organic layers are washed with water, 5% aqueous Na2CO3, and water again, then dried (anhydrous sodium sulfate) and evaporated to an oil residue. The oil is purified by bulb-to-bulb vacuum distillation to provide 14.2 g (74%) to methyl 5-methoxy-3 -(1-methylethoxy)-2-benzofurancarboxylate, suitable for further synthesis; mp=55°-63° C.

Workup

  1. additionis added dropwise
  2. stirringAfter stirring at room temperature for 48 hours
  3. extractionThe mixture is extracted with dichloromethane
  4. washthe combined organic layers are washed with water, 5% aqueous Na2CO3, and water again
  5. dry with materialdried (anhydrous sodium sulfate)
  6. customevaporated to an oil residue
  7. distillationThe oil is purified by bulb-to-bulb vacuum distillation

Sources & evidence

ORD record
ord-9fdeee60049244a0b1aad61df65caef5
Source dataset
uspto-grants-1994_09
Patent number
US05350748

Reaction notes

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