Tetrahydrofuran → HCID 66783589, compound

HRID 1096810Notes

Reaction equation

HRID 1096810 reaction equation
C([C:5]1[N:6]=[CH:7][S:8][CH:9]=1)CC=C.C[N+]1([O-])CC[O:14]CC1.[O-]S([O-])=O.[Na+].[Na+].[CH2:24]1[CH2:28][O:27][CH2:26][CH2:25]1>CC(O)(C)C.O.[Cl-].[Na+].O.O=[Os](=O)(=O)=O>[S:8]1[CH:9]=[C:5]([CH2:28][CH2:24][CH:25]([OH:14])[CH2:26][OH:27])[N:6]=[CH:7]1

Participants

9

Reactant 4

HCID 8028TetrahydrofuranHCID 24437Sodium SulfiteHCID 82029Methyl morpholine oxideHCID 45121686HCID 45121686, compound

Product 1

HCID 66783589HCID 66783589, compoundYield 63%

Reagents, catalysts & solvents 4

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×HCID 6386tert-ButanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a sol. of 4-but-3-enylthiazole (2.07 g, 14.9 mmol) in THF (20 mL), tBuOH (10 mL) and water (5 mL), was added NMO (2.21 g, 16.4 mmol). OsO4 (2.5 wt % in tBuOH, 3.74 mL, 0.298 mmol) was added. The sol. was stirred for 3 h. A sol. of Na2SO3 (1.5 g) in 20 mL water was added. Brine (200 mL) was added and this mixture was extracted with EtOAc (4×). The combined org. phases were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (EtOAc/heptane 3:7→1:1→3:1→EtOAc→MeOH/EtOAc 1:9) yielded the title compound (1.63 g, 63%).

Workup

  1. extractionthis mixture was extracted with EtOAc (4×)
  2. dry with materialphases were dried over MgSO4
  3. filtrationfiltered
  4. customthe solvents were removed under reduced pressure
  5. customPurification of the residue by FC (EtOAc/heptane 3:7→1:1→3:1→EtOAc→MeOH/EtOAc 1:9)

Sources & evidence

ORD record
ord-702ff6a4b26c40b7b2d29ae021cddcbb
Source dataset
uspto-grants-2012_03
Patent number
US08138340B2

Reaction notes

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