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

HRID 1493302Notes

Reaction equation

HRID 1493302 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-f70d9fcee4aa4ad69e562896626934e9
Source dataset
uspto-grants-1991_06
Patent number
US05021414

Reaction notes

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