Acetic Acid → HCID 20559413, compound

HRID 1659574Notes

Reaction equation

HRID 1659574 reaction equation
[BH4-].[Na+].[CH:3]([C:5]1[O:9][C:8]([CH2:10][S:11][CH2:12][CH2:13][N:14]2[C:22](=[O:23])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]2=[O:24])=[CH:7][CH:6]=1)=[O:4].C(O)(=O)C>CO>[OH:4][CH2:3][C:5]1[O:9][C:8]([CH2:10][S:11][CH2:12][CH2:13][N:14]2[C:15](=[O:24])[C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:22]2=[O:23])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 20492177HCID 20492177, compound

Product 1

HCID 20559413HCID 20559413, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (165 mg) was added in portions over a period of 10 mins to a solution of 2-[2-[(5-formyl-2-furanylmethyl)thio]ethyl]-1H-isoindole-1,3(2H)-dione (5.0 g) in methanol (100 ml) at 0° C. After stirring for 45 mins, acetic acid (1 ml) was added and the mixture evaporated. Water (100 ml) was added and the solid that precipitated extracted into ethyl acetate (2×150 ml). The ethyl acetate extracts were dried (magnesium sulphate) and evaporated yielding an oil which solidified on trituration in light petroleum (b.p. 60°-80° C.). Crystallisation from methyl acetate-light petroleum (b.p. 60°-80° C.) afforded the title compound as a light, white solid (4.05 g) m.p. 82.5°-84° C.

Workup

  1. customthe mixture evaporated
  2. additionWater (100 ml) was added
  3. customthe solid that precipitated
  4. extractionextracted into ethyl acetate (2×150 ml)
  5. dry with materialThe ethyl acetate extracts were dried (magnesium sulphate)
  6. customevaporated
  7. customyielding an oil which
  8. customCrystallisation from methyl acetate-light petroleum (b.p. 60°-80° C.)

Sources & evidence

ORD record
ord-7a2b480389f443f387d48d6503f397a1
Source dataset
uspto-grants-1981_12
Patent number
US04304780

Reaction notes

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