Hydrochloric Acid → HCID 178519444, compound

HRID 1064837Notes

Reaction equation

HRID 1064837 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[SH:11][C:12]1[O:13][C:14]2[C:20]([C:21](OC)=[O:22])=[CH:19][CH:18]=[CH:17][C:15]=2[N:16]=1.Cl>C1(C)C=CC=CC=1.C1COCC1>[OH:22][CH2:21][C:20]1[C:14]2[O:13][C:12]([SH:11])=[N:16][C:15]=2[CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 21225700Diisobutylaluminumhydride3×HCID 178497587HCID 178497587, compound

Product 1

HCID 178519444HCID 178519444, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A 1.0M solution of diisobutyl aluminum hydride in toluene (10 ml) was slowly dropped, under argon atmosphere at −78° C., into a solution of 2-mercapto-7-methoxycarbonylbenzoxazole (1.1 g, 5.0 mmol) in THF (20 ml) followed by stirring for 30 minutes. At that temperature, a 1.0M solution of diisobutyl aluminum hydride in toluene (5 ml) was slowly dropped thereinto followed by stirring for 30 minutes. After cooling, diluted hydrochloric acid was added to the reaction mixture to decompose the excessive diisobutyl aluminum hydride, after then extracted with ethyl acetate. The organic layer was washed with diluted hydrochloric acid solution and a saturated sodium chloride solution, dried over sodium sulfate and the solvent was evaporated therefrom. The resulting crude product was recrystallized from hexane-acetone-methanol to provide 848 mg (yield 94%) of 7-hydroxymethyl-2-mercaptobenzooxazole as colorless needles.

Workup

  1. stirringby stirring for 30 minutes
  2. temperatureAfter cooling
  3. extractionafter then extracted with ethyl acetate
  4. washThe organic layer was washed with diluted hydrochloric acid solution
  5. dry with materiala saturated sodium chloride solution, dried over sodium sulfate
  6. customthe solvent was evaporated
  7. customThe resulting crude product was recrystallized from hexane-acetone-methanol

Sources & evidence

ORD record
ord-c499f219d52b42b4940a2534e8162db4
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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