Oxolane--water (1/1) → HCID 66745597, compound

HRID 1467152Notes

Reaction equation

HRID 1467152 reaction equation
[CH:1]1([O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[C:9]=2[C:10]#[N:11])[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.C1C[O:22]CC1.[OH2:24]>O=[Os](=O)(=O)=O>[OH:24][CH:2]1[CH:3]([OH:22])[CH2:4][CH2:5][CH2:6][CH:1]1[O:7][C:8]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[C:9]=1[C:10]#[N:11]

Participants

4

Reactant 2

HCID 21881883Oxolane--water (1/1)HCID 66747185HCID 66747185, compound

Product 1

HCID 66745597HCID 66745597, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

To a solution of 2-(cyclohex-2-en-1-yloxy)-6-nitrobenzonitrile (Example 133e, 5.3 g, 21.7 mmol) in THF/H2O (1:1 by volume, 110 mL) was added OsO4 (110.3 mg, 0.434 mmol) at room temperature. After it was stirred for 30 minutes, NaClO3 (2.71 g, 26.04 mmol) was added in small portions over a period of 1 h, and the reaction mixture was stirred at room temperature for 48 h. The reaction was carefully quenched with aqueous sodium bisulfite solution, and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried over MgSO4, filtered, and evaporated. The residue was purified by chromatography on silica gel eluting with 80-100% EtOAc in hexanes to give the title compound as a brown solid (3.88 g, 64%). MS 279 (MH+).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 48 h
  2. customThe reaction was carefully quenched with aqueous sodium bisulfite solution
  3. extractionextracted with EtOAc (3×)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by chromatography on silica gel eluting with 80-100% EtOAc in hexanes

Sources & evidence

ORD record
ord-f7538e52b4e24b499fd024742496b09a
Source dataset
uspto-grants-2015_04
Patent number
US09000054B2

Reaction notes

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