Potassium tert-butoxide → HCID 20163695, compound

HRID 256346Notes

Reaction equation

HRID 256346 reaction equation
CC(C)([O-])C.[K+].[CH3:7][O:8][C:9]1[C:17]2[O:16][C:15]([C:18]([O:20]C)=[O:19])=[C:14]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:13]=2[CH:12]=[CH:11][CH:10]=1>CS(C)=O>[CH3:7][O:8][C:9]1[C:17]2[O:16][C:15]([C:18]([OH:20])=[O:19])=[C:14]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:13]=2[CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 86741845HCID 86741845, compound

Product 1

HCID 20163695HCID 20163695, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 1.34 g (0.012 mole) of potassium tert-butoxide in 50 ml of dimethyl sulfoxide (under a nitrogen atmosphere) is treated with 2.3 g (0.0066 mole) of crude 7-methoxy-3-(nonyloxy)-2-benzofurancarboxylic acid, methyl ester. After stirring at room temperature for three hours, the mixture is added to 400 g of ice/water. The new mixture is extracted with dichloromethane (3×250 ml), and the aqueous layer is cooled in ice and acidified with 4.0 N hydrochloric acid. The semisolid precipitate that forms is removed by extracting with dichloromethane (3×150 ml). The combined extracts are backwashed with water (2×200 ml), dried (anhydrous sodium sulfate), and evaporated (vacuum) to yield 7-methoxy-3-(nonyloxy)-2-benzofurancarboxylic acid (0.7 g; 32% yield) as an oil. The crude oil is converted to the corresponding 2-benzofurancarbamoyltetrazole without further purification.

Workup

  1. extractionThe new mixture is extracted with dichloromethane (3×250 ml)
  2. temperaturethe aqueous layer is cooled in ice
  3. customThe semisolid precipitate that forms is removed
  4. extractionby extracting with dichloromethane (3×150 ml)
  5. dry with materialdried (anhydrous sodium sulfate)
  6. customevaporated (vacuum)

Sources & evidence

ORD record
ord-6829c81382db4b539b3a1f0e3c3e8c43
Source dataset
uspto-grants-1987_10
Patent number
US04703053

Reaction notes

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