Sulfolane → HCID 85977416, compound

HRID 485423Notes

Reaction equation

HRID 485423 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[CH:14](Br)[CH2:13][C:12]3[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=3[S:10][C:9]=2[CH:20]=1)=[O:4].S1(CCCC1)(=O)=O.[BH4-].[Na+]>>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[CH2:14][CH2:13][C:12]3[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=3[S:10][C:9]=2[CH:20]=1)=[O:4]

Participants

4

Reactant 3

HCID 31347SulfolaneHCID 4311764Sodium borohydrideHCID 13151857HCID 13151857, compound

Product 1

HCID 85977416HCID 85977416, compound

Procedure

13.6 G. methyl-11-bromo-10,11-dihydrodibenzo[b,f]thiepin-3-carboxylate is suspended in 150 cc. sulfolane and to the mechanically stirred mixture 7.18 g. sodium borohydride is added in portions over one hour. The foamy mixture is stirred an additional half hour. The mixture is diluted with 1.5 l. of water and extracted with ether. The organic layer is washed with water, dried, evaporated, and the residual oil is chromatographed on silica gel. Elution with benzene affords 8.1 g. of the pure oily material.

Workup

  1. additionThe mixture is diluted with 1.5 l
  2. extractionof water and extracted with ether
  3. washThe organic layer is washed with water
  4. customdried
  5. customevaporated
  6. customthe residual oil is chromatographed on silica gel
  7. washElution with benzene
  8. customaffords 8.1 g

Sources & evidence

ORD record
ord-9a42ff19775f42698472e2fab35d4114
Source dataset
uspto-grants-1985_08
Patent number
US04536507

Reaction notes

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