Sodium periodate → (1RS, 2RS)-1-(9-n-heptylsulphinylnonyl)-2-p-hydroxyphenyl-1,2,3,4-tetrahydronaphth-6-ol

HRID 569633Notes

Reaction equation

HRID 569633 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[CH2:7]([S:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH:24]1[C:33]2[C:28](=[CH:29][C:30]([OH:34])=[CH:31][CH:32]=2)[CH2:27][CH2:26][CH:25]1[C:35]1[CH:40]=[CH:39][C:38]([OH:41])=[CH:37][CH:36]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]>O.CO>[CH2:7]([S:14]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH:24]1[C:33]2[C:28](=[CH:29][C:30]([OH:34])=[CH:31][CH:32]=2)[CH2:27][CH2:26][CH:25]1[C:35]1[CH:40]=[CH:39][C:38]([OH:41])=[CH:37][CH:36]=1)=[O:2])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 2

HCID 23667635Sodium periodateHCID 86742065(1RS, 2RS)-1-(9-n-heptylthiononyl)-2-p-hydroxyphenyl-1,2,3,4-tetrahydronaphth-6-ol

Product 1

HCID 70447526(1RS, 2RS)-1-(9-n-heptylsulphinylnonyl)-2-p-hydroxyphenyl-1,2,3,4-tetrahydronaphth-6-ol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of sodium metaperiodate (0.026 g.) in water (2 ml.) was added to a stirred solution of (1RS, 2RS)-1-(9-n-heptylthiononyl)-2-p-hydroxyphenyl-1,2,3,4-tetrahydronaphth-6-ol (Example 7; 0.052 g.) in methanol (20 ml.) and the mixture was stirred for 16 hours. The methanol was removed by evaporation, the residue was extracted three times with ethyl acetate (10 ml. each time) and the combined extracts were washed with water, dried and evaporated to dryness. The residue was purified by chromatography on a silica gel column using a 2:1 v/v mixture of toluene and ethyl acetate as eluant, and there was thus obtained as an oil (1RS, 2RS)-1-(9-n-heptylsulphinylnonyl)-2-p-hydroxyphenyl-1,2,3,4- tetrahydronaphth-6-ol, the structure of which was confirmed by proton magnetic resonance and mass spectroscopy.

Workup

  1. customThe methanol was removed by evaporation
  2. extractionthe residue was extracted three times with ethyl acetate (10 ml
  3. washeach time) and the combined extracts were washed with water
  4. customdried
  5. customevaporated to dryness
  6. customThe residue was purified by chromatography on a silica gel column
  7. additiona 2:1 v/v mixture of toluene and ethyl acetate as eluant

Sources & evidence

ORD record
ord-d518d54d511e4fe7a12ddefa64ac3416
Source dataset
uspto-grants-1988_03
Patent number
US04732912

Reaction notes

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