1-Hexanethiol → 1-(10-Hexylthiodecyl)-2-p-hydroxyphenylind-1-en-5-ol

HRID 1200094Notes

Reaction equation

HRID 1200094 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[C:20]2[C:15](=[CH:16][C:17]([O:21]C)=[CH:18][CH:19]=2)[CH2:14][C:13]=1[C:23]1[CH:28]=[CH:27][C:26]([O:29]C)=[CH:25][CH:24]=1.[CH2:31]([SH:37])[CH2:32][CH2:33][CH2:34][CH2:35][CH3:36].[H-].[Na+]>CN(C)C=O>[CH2:31]([S:37][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[C:20]2[C:15](=[CH:16][C:17]([OH:21])=[CH:18][CH:19]=2)[CH2:14][C:13]=1[C:23]1[CH:24]=[CH:25][C:26]([OH:29])=[CH:27][CH:28]=1)[CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

Participants

5

Reactant 3

HCID 81061-HexanethiolHCID 24758Sodium hydrideHCID 86120592HCID 86120592, compound

Product 1

HCID 861205951-(10-Hexylthiodecyl)-2-p-hydroxyphenylind-1-en-5-ol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 1-(10-bromodecyl)-5-methoxy-2-p-methoxyphenylind-1-ene (0.24 g.) in dimethylformamide (1 ml.) was added to a stirred solution of hexanethiol (0.07 g.) and sodium hydride (0.029 g. of a 50% dispersion in mineral oil from which the oil had been washed with petroleum ether) in dimethylformamide which has been stirred at laboratory temperature under an atmosphere of argon for 15 minutes, and the mixture was heated at 60° C. for 2 hours, cooled and water (5 ml.) was added. The mixture was extracted 3 times with ethyl acetate (5 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 1:1 v/v mixture of toluene and petroleum ether (b.p. 60°-80° C.) as eluant. The methoxy groups were removed by treatment with boron tribromide in a similar manner to that described in Example 7, and the residue was purified by chromatography on a silica gel column using a 9:1 v/v mixture of toluene and ethyl acetate as eluant. There was thus obtained as an oil 1-(10-hexylthiodecyl)-2-p-hydroxyphenylind-1-en-5-ol, the structure of which was confirmed by proton magnetic resonance and mass spectroscopy.

Workup

  1. washof a 50% dispersion in mineral oil from which the oil had been washed with petroleum ether) in dimethylformamide which
  2. temperaturecooled
  3. additionwater (5 ml.) was added
  4. extractionThe mixture was extracted 3 times with ethyl acetate (5 ml
  5. washeach time) and the combined extracts were washed with water
  6. customdried
  7. customevaporated to dryness
  8. customThe residue was purified by chromatography on a silica gel column
  9. additiona 1:1 v/v mixture of toluene and petroleum ether (b.p. 60°-80° C.) as eluant
  10. customThe methoxy groups were removed by treatment with boron tribromide in a similar manner to that
  11. customthe residue was purified by chromatography on a silica gel column
  12. additiona 9:1 v/v mixture of toluene and ethyl acetate as eluant

Sources & evidence

ORD record
ord-d1a24ffce2c94766a3eabafd72a70a1b
Source dataset
uspto-grants-1990_02
Patent number
US04904661

Reaction notes

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