Triethylamine → HCID 53950019, compound

HRID 486719Notes

Reaction equation

HRID 486719 reaction equation
[OH:1][CH:2]([CH2:14][CH2:15][O:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][O:18]1)[CH2:3][CH:4]([CH2:12]O)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].C(N(CC)CC)C.[S:30](Cl)([CH3:33])(=[O:32])=[O:31]>C(Cl)Cl>[S:30]([O:1][CH:2]([CH2:14][CH2:15][O:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][O:18]1)[CH2:3][C:4](=[CH2:12])[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])([CH3:33])(=[O:32])=[O:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 54082115HCID 54082115, compound

Product 1

HCID 53950019HCID 53950019, compoundYield 66.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of tert-butyl 4-hydroxy-2-hydroxymethyl-6-tetrahydropyranyloxyhexanoate (0.28 g) and triethylamine (0.56 g) in methylene chloride (20 ml), mesylchloride (0.56 g) dissolved in methylene chloride (10 ml) was added dropwise under nitrogen atmosphere and ice-cooling. The mixture was stirred for 2 hours at room temperature and concentrated in vacuo. Saturated aqueous sodium bicarbonate solution was added to the oily residue and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate solution, 1N hydrochloric acid, water and saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo. The oily residue was dissolved in benzene (20 ml), and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.2 g) was added to the solution. The mixture was stirred for 3 hours. Aqueous citric acid solution was added to the mixture and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate solution, water and saturated sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo. The oily residue was purified by a silica gel column chromatography to give 0.22 g (31%) of tert-butyl 4-mesyloxy-2-methylene-6-tetrahydropyranyloxyhexanoate.

Workup

  1. additionwas added dropwise under nitrogen atmosphere
  2. temperatureice-cooling
  3. concentrationconcentrated in vacuo
  4. additionSaturated aqueous sodium bicarbonate solution was added to the oily residue
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution, 1N hydrochloric acid, water and saturated aqueous sodium chloride solution
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. dissolutionThe oily residue was dissolved in benzene (20 ml)
  10. addition1,8-diazabicyclo[5.4.0]undec-7-ene (0.2 g) was added to the solution
  11. stirringThe mixture was stirred for 3 hours
  12. additionAqueous citric acid solution was added to the mixture
  13. extractionextracted with ethyl acetate
  14. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution, water and saturated sodium chloride solution
  15. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  16. concentrationconcentrated in vacuo
  17. customThe oily residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-5b2870c90c8141c1a9eead9dcc48ba9a
Source dataset
uspto-grants-1994_03
Patent number
US05292767

Reaction notes

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