Water → HCID 23043533, compound

HRID 256502Notes

Reaction equation

HRID 256502 reaction equation
[H-].[Na+].C[C:4]1([CH3:11])[O:8][CH:7]([CH2:9][OH:10])[CH2:6][O:5]1.[CH3:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]CCS(C1C=CC(C)=CC=1)(=O)=O.O>CN(C)C=O>[CH3:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:11][CH2:4][O:5][CH2:6][CH:7]([OH:8])[CH2:9][OH:10]

Participants

6

Reactant 4

HCID 962WaterHCID 7528SolketalHCID 24758Sodium hydrideHCID 23043536HCID 23043536, compound

Product 1

HCID 23043533HCID 23043533, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 9.01 g of unwashed 50% sodium hydride in 100 ml of dimethyformamide was added, dropwise over one hour, 22.06 g of solketal. After cooling in an ice bath a solution of 42 g of 1-[[8-[2-(2-methoxyethoxy)-ethoxy]octyl]sulfonyl]-4-methylbenzene in 25 ml of dimethylformamide was added. This mixture was stirred for 2 days, then water was added and the mixture extracted with ether. The ether extract was dried and the solvent removed. The residue was refluxed for one hour in a mixture of 175 ml of methanol, 25 ml of water and 1.25 ml of concentrated sulfuric acid. The methanol was removed, saturated aqueous sodium chloride added and the mixture extracted with ethyl acetate. The organic extract was dried, the solvent removed and the residue purified by HPLC, eluting with ethyl acetate, giving 14.7 g of the desired compound as an oil.

Workup

  1. additionwas added, dropwise over one hour
  2. additionwas added
  3. extractionthe mixture extracted with ether
  4. extractionThe ether extract
  5. customwas dried
  6. customthe solvent removed
  7. temperatureThe residue was refluxed for one hour in a mixture of 175 ml of methanol, 25 ml of water and 1.25 ml of concentrated sulfuric acid
  8. customThe methanol was removed
  9. additionsaturated aqueous sodium chloride added
  10. extractionthe mixture extracted with ethyl acetate
  11. extractionThe organic extract
  12. customwas dried
  13. customthe solvent removed
  14. customthe residue purified by HPLC
  15. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-e245f7c21ae34828a145ff11d4b420e9
Source dataset
uspto-grants-1987_10
Patent number
US04703130

Reaction notes

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