Diethyl Ether → HCID 54272425, compound

HRID 2226587Notes

Reaction equation

HRID 2226587 reaction equation
[H-].[Na+].[CH:3]1([CH2:8][OH:9])[CH2:7][CH2:6][CH2:5][CH2:4]1.CC1C=CC=CC=1S(O[CH2:21][C@H:22]1[CH2:26][O:25][C:24]([CH3:28])([CH3:27])[O:23]1)(=O)=O.CCOCC>CN(C)C=O.[Cl-].[Na+].O>[CH:3]1([CH2:8][O:9][CH2:21][C@H:22]2[CH2:26][O:25][C:24]([CH3:28])([CH3:27])[O:23]2)[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 77195CyclopentanemethanolHCID 117833485HCID 117833485, compound

Product 1

HCID 54272425HCID 54272425, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Sodium hydride (0.63 g, 26.3 mmol) and cyclopentanemethanol (2.8 ml, 25.9 mmol) in dimethylformamide were heated at 50° for 30 min. The reaction mixture was cooled to 20° and (R)-2,2-dimethyl-1,3-dioxolane-4-methanol 4-methylbenzenesulphonate (5.0 g, 17.5 mmol) added. The reaction mixture was heated at 50° for 30 min and left at 20° for 18 h. Ether and brine were added, the organic layer dried (Na2SO4) and the solvent evaporated to give the sub-title ether (3.0 g).

Workup

  1. temperatureThe reaction mixture was cooled to 20°
  2. temperatureThe reaction mixture was heated at 50° for 30 min
  3. dry with materialthe organic layer dried (Na2SO4)
  4. customthe solvent evaporated
  5. customto give the sub-title ether (3.0 g)

Sources & evidence

ORD record
ord-65335478ab3e4f5fbd7844dde4357f30
Source dataset
uspto-grants-1994_09
Patent number
US05348978

Reaction notes

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