Methyl chloroformate → Carbonic acid 3-(2',4'-dichloro-4-ethylbiphen-3-yl)-4-oxo-bicyclo[3.2.1]oct-2-en-2-yl ester methyl ester

HRID 72306Notes

Reaction equation

HRID 72306 reaction equation
[Cl:1][C:2]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:3]=1[C:4]1[CH:5]=[CH:6][C:7]([CH2:20][CH3:21])=[C:8]([CH:10]2[C:16](=[O:17])[CH:15]3[CH2:18][CH:12]([CH2:13][CH2:14]3)[C:11]2=[O:19])[CH:9]=1.C(N(CC)CC)C.Cl[C:35]([O:37][CH3:38])=[O:36]>ClCCl>[CH3:38][O:37][C:35](=[O:36])[O:17][C:16]1[CH:15]2[CH2:18][CH:12]([C:11](=[O:19])[C:10]=1[C:8]1[CH:9]=[C:4]([C:3]3[CH:22]=[CH:23][C:24]([Cl:26])=[CH:25][C:2]=3[Cl:1])[CH:5]=[CH:6][C:7]=1[CH2:20][CH3:21])[CH2:13][CH2:14]2

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 912810483-(2',4'-Dichloro-4-ethylbiphen-3-yl)bicyclo[3.2.1]octane-2,4-dione

Product 1

HCID 76807988Carbonic acid 3-(2',4'-dichloro-4-ethylbiphen-3-yl)-4-oxo-bicyclo[3.2.1]oct-2-en-2-yl ester methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(2′,4′-dichloro-4-ethylbiphen-3-yl)-bicyclo[3.2.1]octane-2,4-dione (0.133 g, 0.34 mmol) in dichloromethane (2 ml) is added triethylamine (0.24 ml, 1.72 mmol) followed by stirring at room temperature for 5 minutes. To this solution is added methyl chloroformate (0.132 ml, 1.72 mmol) dropwise, then the mixture is left to stand overnight. The reaction mixture is concentrated in vacuo to afford a crude solid which is purified by flash column chromatography on silica gel (100% to 70% hexane/ethyl acetate eluant ratio) to afford carbonic acid 3-(2′,4′-dichloro-4-ethylbiphen-3-yl)-4-oxo-bicyclo[3.2.1]oct-2-en-2-yl ester methyl ester.

Workup

  1. waitthe mixture is left
  2. waitto stand overnight
  3. concentrationThe reaction mixture is concentrated in vacuo
  4. customto afford a crude solid which
  5. customis purified by flash column chromatography on silica gel (100% to 70% hexane/ethyl acetate eluant ratio)

Sources & evidence

ORD record
ord-c009799bd0b448ae8de99f5d4e0eb69a
Source dataset
uspto-grants-2014_09
Patent number
US08828908B2

Reaction notes

Loading…