Acetate → HCID 20185127, compound

HRID 2309388Notes

Reaction equation

HRID 2309388 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][C:8]([OH:15])=[C:9]([CH2:12][CH:13]=[CH2:14])[CH:10]=2)[CH2:5][C:4]1=[O:16])[CH3:2].C([O-])(=O)C.[OH-].[Na+].[BH4-].[Na+]>C(OCC)C.O.O1CCCC1>[CH3:14][CH:13]1[O:15][C:8]2=[CH:7][C:6]3[CH2:5][C:4](=[O:16])[N:3]([CH2:1][CH3:2])[C:11]=3[CH:10]=[C:9]2[CH2:12]1

Participants

8

Reactant 4

HCID 175AcetateHCID 14798Sodium Hydroxide2×HCID 4311764Sodium borohydrideHCID 13603422HCID 13603422, compound

Product 1

HCID 20185127HCID 20185127, compoundYield 28%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6.0 g. (27.6 mmoles) of 1-ethyl-5-hydroxy-6-allyloxindole in 105 ml. of tetrahydrofuran was added 8.79 g. (27.6 mmoles) of mecuric acetate, and the reaction stirred for 1.5 hours. The mixture was diluted with 29 ml. of 3N sodium hydroxide solution followed by the addition of 522 mg. (13.7 mmoles) of sodium borohydride in 29 ml. of 3N sodium hydroxide solution. The mixture was stirred for 1 hour and was then diluted with diethyl ether and water. The organic phase was washed with water and a saturated brine solution, and then dried over magnesium sulfate. Evaporation of the solvent and chromatographing of the residue on 100 g. of silica gel, using diethyl ether-hexane (1:1, v:v) as the eluent, gave 1.68 g. (28% yield) of the desired product.

Workup

  1. additionThe mixture was diluted with 29 ml
  2. washThe organic phase was washed with water
  3. dry with materiala saturated brine solution, and then dried over magnesium sulfate
  4. customEvaporation of the solvent and chromatographing of the residue on 100 g
  5. customgave 1.68 g

Sources & evidence

ORD record
ord-88c10bc3d6554369a9f1c50b2c9ac350
Source dataset
uspto-grants-1987_09
Patent number
US04695571

Reaction notes

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