Tetrahydrofuran → HCID 12017162, compound

HRID 277883Notes

Reaction equation

HRID 277883 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([CH2:13][C:14]([CH3:16])=C)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C[O:20]CC1>O.CCOC(C)=O.O=[Os](=O)(=O)=O>[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([CH2:13][C:14](=[O:20])[CH3:16])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 8028TetrahydrofuranHCID 12017161HCID 12017161, compound

Product 1

HCID 12017162HCID 12017162, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalyst2×HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a rapidly stirred solution of 1-4 (7.0 g, 33 mmol) in THF (200 mL) and H2O (150 mL) was added NaIO4 (21 g, 100 mmol) followed by addition of OsO4 (10 mL; 2.5% solution). After 16 hrs, an additional amount of OsO4 (10 mL) was added, and the reaction was stirred for 6 hrs. The reaction was diluted with EtOAc, washed with sat. NaHCO3 and brine, dried (MgSO4), and concentrated to give 1-5 as a brown oil.

Workup

  1. washwashed with sat. NaHCO3 and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-576ef43720da43cb81f6ed894e3dae1f
Source dataset
uspto-grants-2002_03
Patent number
US06358970B1

Reaction notes

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