HCID 14327180, compound → HCID 14327181, compound

HRID 1111548Notes

Reaction equation

HRID 1111548 reaction equation
[CH2:1]([NH:3][S:4]([C:7]1[CH:12]=[CH:11][C:10]([CH:13]([C:15]2[CH:24]=[CH:23][C:22]3[C:21]([CH3:26])([CH3:25])[CH2:20][CH2:19][C:18]([CH3:28])([CH3:27])[C:17]=3[CH:16]=2)[OH:14])=[CH:9][CH:8]=1)(=[O:6])=[O:5])[CH3:2].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[CH2:1]([NH:3][S:4]([C:7]1[CH:8]=[CH:9][C:10]([C:13]([C:15]2[CH:24]=[CH:23][C:22]3[C:21]([CH3:26])([CH3:25])[CH2:20][CH2:19][C:18]([CH3:27])([CH3:28])[C:17]=3[CH:16]=2)=[O:14])=[CH:11][CH:12]=1)(=[O:5])=[O:6])[CH3:2]

Participants

4

Reactant 2

HCID 14327180HCID 14327180, compoundHCID 131709961Jones' reagent

Product 1

HCID 14327181HCID 14327181, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution, stirred at ambient temperature, of 2 g of N-ethyl 4-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl) hydroxymethyl] phenyl sulfonamide, prepared in Example III, in 100 cm3 of acetone, there is added the Jones reagent prepared in accordance with Example II. The reaction mixture is then treated under the same conditions. The carbonyl derivative is purified by passage through a silica gel chromatography column. It is eluted with a 4/1 hexane/ethyl acetate mixture and recrystallized in a hexane/isopropyl ether mixture. 1.5 g of N-ethyl 4-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl) carbonyl]phenylsulfonamide are obtained.

Workup

  1. customprepared in accordance with Example II
  2. additionThe reaction mixture is then treated under the same conditions
  3. customThe carbonyl derivative is purified by passage through a silica gel chromatography column
  4. washIt is eluted with a 4/1 hexane/ethyl acetate mixture
  5. customrecrystallized in a hexane/isopropyl ether mixture

Sources & evidence

ORD record
ord-87b0dd6581874fda9fbffdadf31203d9
Source dataset
uspto-grants-1990_12
Patent number
US04980509

Reaction notes

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