Sodium hydride → HCID 10561223, compound

HRID 355550Notes

Reaction equation

HRID 355550 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([CH2:11][CH2:12][C@H:13]([O:16]S(C)(=O)=O)[CH2:14]O)=[CH:9][CH:10]=1)=[O:5])[CH3:2].[H-].[Na+]>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([CH2:11][CH2:12][C@@H:13]2[CH2:14][O:16]2)=[CH:9][CH:10]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 54255716HCID 54255716, compound

Product 1

HCID 10561223HCID 10561223, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred, ice-cold solution of 559 mg (1.73 mmol) of the mesylate (18) in 10 ml of THF was added 76 mg (1.90 mmol) of a 60% dispersion of sodium hydride (NaH) in mineral oil. After 1 hour, the ice bath was removed and the reaction was stirred at room temperature. After stirring for 18 hours, another 35 mg (0.88 mmol) of a 60% dispersion of NaH was added. After 4 days of stirring, the reaction mixture was diluted with EtOAc, washed with 0.5N HCl and then with saturated NaCl, dried (MgSO4), and concentrated under reduced pressure. The resulting crude residue was flash-chromatographed on silica gel, eluting CH2Cl2. Consequently, 322 mg (82%) of the desired epoxide (19) was obtained as a colorless oil.

Workup

  1. customthe ice bath was removed
  2. stirringAfter stirring for 18 hours
  3. additionanother 35 mg (0.88 mmol) of a 60% dispersion of NaH was added
  4. stirringAfter 4 days of stirring
  5. additionthe reaction mixture was diluted with EtOAc
  6. washwashed with 0.5N HCl
  7. dry with materialwith saturated NaCl, dried (MgSO4)
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting crude residue was flash-chromatographed on silica gel
  10. washeluting CH2Cl2

Sources & evidence

ORD record
ord-c1221f436b3c4f66ae21e355e4435d3d
Source dataset
uspto-grants-1998_11
Patent number
US05831100

Reaction notes

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