Pyridine → HCID 10989162, compound

HRID 2234258Notes

Reaction equation

HRID 2234258 reaction equation
[CH:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N1C=CC=CC=1.Cl[C:15]([O:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1)=[O:16]>C1COCC1>[C:15](=[O:16])([O:17][C:18]1[CH:19]=[CH:20][C:21]([N+:24]([O-:26])=[O:25])=[CH:22][CH:23]=1)[O:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7966CyclohexanolHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 10989162HCID 10989162, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of cyclohexanol (1.0 g, 10 mmol) in THF (20 mL) at 0° C. was added pyridine (0.97 mL, 12 mmol). After 5 min stirring under N2, a solution of 4-nitrophenyl chloroformate (2.2 g, 11 mmol) in THF (15 mL) was added slowly. After addition, the reaction mixture was stirred at 0° C. for 30 min, and then at RT for 3 h. The precipitate was filtered, the filtrate was concentrated. The resulting residue was chromatographed (40 g silica gel) eluting with EtOAc (0-20%) in hexanes to give the title compound (2.4 g, 91%) as a white solid.

Workup

  1. additionAfter addition
  2. stirringthe reaction mixture was stirred at 0° C. for 30 min
  3. waitat RT for 3 h
  4. filtrationThe precipitate was filtered
  5. concentrationthe filtrate was concentrated
  6. customThe resulting residue was chromatographed (40 g silica gel)
  7. washeluting with EtOAc (0-20%) in hexanes

Sources & evidence

ORD record
ord-80284937c0cb427aa109ee3ab8e6e4f7
Source dataset
uspto-grants-2010_05
Patent number
US07709647B2

Reaction notes

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