Water → Carbonic acid, cyclobutyl 4-nitrophenyl ester

HRID 1184693Notes

Reaction equation

HRID 1184693 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:3].[CH:14]1([OH:18])[CH2:17][CH2:16][CH2:15]1.N1C=CC=CC=1.O>ClCCl>[N+:11]([C:8]1[CH:7]=[CH:6][C:5]([O:4][C:2](=[O:3])[O:18][CH:14]2[CH2:17][CH2:16][CH2:15]2)=[CH:10][CH:9]=1)([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 76218CyclobutanolHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 22708352Carbonic acid, cyclobutyl 4-nitrophenyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 4-nitrophenyl chloroformate (6.00 g) in dichloromethane (12 mL) is added dropwise to an ice-cooled mixture of cyclobutanol (2.00 g), and pyridine (2.4 mL) in dichloromethane (10 mL). The resulting mixture is stirred over night at room temperature. Water and dichloromethane are added and the organic phase is separated, washed with brine and dried over MgSO4. The solvent is evaporated leaving the title compound as an oil, which is used without further purification. Yield: 6.61 g (crude); LC (method 2): tR=1.30 min; Mass spectrum (ESI+): m/z=260 [M+Na]+.

Workup

  1. temperaturecooled
  2. customthe organic phase is separated
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. customThe solvent is evaporated

Sources & evidence

ORD record
ord-e6e838ba61ae4ab2a70244927987f954
Source dataset
uspto-grants-2014_03
Patent number
US08669271B2

Reaction notes

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