Acetone → HCID 13744912, compound

HRID 34323Notes

Reaction equation

HRID 34323 reaction equation
[C:1]([C:5]1[O:6][C:7]2[CH:15]=[C:14]([SH:16])[CH:13]=[CH:12][C:8]=2[C:9](=[O:11])[CH:10]=1)(OC)=[O:2].O.[BH4-].[Na+].CC(C)=O>CO>[OH:2][CH2:1][C:5]1[O:6][C:7]2[CH:15]=[C:14]([SH:16])[CH:13]=[CH:12][C:8]=2[C:9](=[O:11])[CH:10]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 4311764Sodium borohydrideHCID 137449112-Carbomethoxy-7-mercapto-4-oxo-4H-1-benzopyran

Product 1

HCID 13744912HCID 13744912, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The ester from Step 4 (3.0 g) in suspension in methanol (20 ml) and water (40 ml) at 0° was stirred vigorously during the portionwise addition of NaBH4 (1.8 g). The mixture was stirred for 2 hours at 5°. Acetone (1 ml) was added followed by acidification with 1N HCl and extraction with methanolchloroform (1:9, 3×50 ml). The combined extracts were dried (Na2SO4), reduced to dryness in vacuo and the residue was recrystallized from methanolethyl acetate to provide the title compound, m.p. 139°-140°.

Workup

  1. extractionfollowed by acidification with 1N HCl and extraction with methanolchloroform (1:9, 3×50 ml)
  2. dry with materialThe combined extracts were dried (Na2SO4)
  3. customthe residue was recrystallized from methanolethyl acetate

Sources & evidence

ORD record
ord-65ac2b1ed89d401b9f8e14a7a24b9b35
Source dataset
uspto-grants-1988_08
Patent number
US04761425

Reaction notes

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