Cyclopentanol → Cyclopentyl 4-nitrophenyl carbonate

HRID 449317Notes

Reaction equation

HRID 449317 reaction equation
[CH:1]1([OH:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[C:8]([O:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1)=[O:9].C(N(CC)CC)C>C(Cl)Cl>[C:8](=[O:9])([O:10][C:11]1[CH:12]=[CH:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=1)[O:6][CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 7298CyclopentanolHCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 54340011Cyclopentyl 4-nitrophenyl carbonateYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of cyclopentanol (0.5 g, 6 mol), p-nitrophenyl chloroformate (1.3 g, 6.4 mmol) in methylene chloride (10 mL) was added triethylamine (1.2 mL, 8.7 mmol). The mixture was stirred at r.t. for 2 h. After removal of solvent, the crude residue was purified by flash chromatography on a silica gel column eluted with 20% EtOAc in hexane to yield the desired product (0.86 g, 59%).

Workup

  1. customAfter removal of solvent
  2. customthe crude residue was purified by flash chromatography on a silica gel column
  3. washeluted with 20% EtOAc in hexane

Sources & evidence

ORD record
ord-aa52e079e502476691102a4e183212c5
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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