Sodium borohydride → HCID 19842209, compound

HRID 280539Notes

Reaction equation

HRID 280539 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13](=[O:14])[C:12]3[S:15][CH2:16][CH2:17][S:18][C:11]=3[C:10]2=[O:19])=[CH:5][CH:4]=1.[BH4-].[Na+]>CO.O1CCCC1>[OH:14][CH:13]1[C:12]2[S:15][CH2:16][CH2:17][S:18][C:11]=2[C:10](=[O:19])[N:9]1[C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 19842238HCID 19842238, compound

Product 1

HCID 19842209HCID 19842209, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

2,3,6,7-Tetrahydro-6-(4-methoxyphenyl)-5H-1,4-dithiino[2,3-C]pyrrole-5,7-dione (8.50 g) was suspended in methanol-tetrahydrofuran (1:1, 80 ml) and, under ice-cooling and stirring, sodium borohydride (0.88 g) was added. The mixture was stirred for about 3 hours and then poured into ice water. After extraction with ethyl acetate, the extract was washed with water, dried (over Na2SO4) and evaporated to give 2,3,6,7-tetrahydro-7-hydroxy-6-(4-methoxyphenyl)-5H-1,4-dithiino[2,3-C]pyrrol-5-one (8.40 g) as crystals.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred for about 3 hours
  3. extractionAfter extraction with ethyl acetate
  4. washthe extract was washed with water
  5. dry with materialdried (over Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-c3411585959c46239f9e69568bf5065a
Source dataset
uspto-grants-1986_05
Patent number
US04590189

Reaction notes

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