Methyl chloroformate → carbonic acid 4-(4'-chloro-4-ethylbiphenyl-3-yl)-2,2,6,6-tetramethyl-5-oxo-5,6-dihydro-2H-pyran-3-yl ester methyl ester

HRID 1191590Notes

Reaction equation

HRID 1191590 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH3:15])=[C:10]([CH:16]3[C:21](=[O:22])[C:20]([CH3:24])([CH3:23])[O:19][C:18]([CH3:26])([CH3:25])[C:17]3=[O:27])[CH:9]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:36]([O:38][CH3:39])=[O:37]>C(Cl)(Cl)Cl>[CH3:39][O:38][C:36](=[O:37])[O:27][C:17]1[C:18]([CH3:26])([CH3:25])[O:19][C:20]([CH3:24])([CH3:23])[C:21](=[O:22])[C:16]=1[C:10]1[CH:9]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[CH:13]=[CH:12][C:11]=1[CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 684877684-(4'-Chloro-4-ethylbiphenyl-3-yl)-2,2,6,6-tetramethylpyran-3,5-dione

Product 1

HCID 58515682carbonic acid 4-(4'-chloro-4-ethylbiphenyl-3-yl)-2,2,6,6-tetramethyl-5-oxo-5,6-dihydro-2H-pyran-3-yl ester methyl esterYield 92.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 4-(4′-chloro-4-ethylbiphenyl-3-yl)-2,2,6,6-tetramethylpyran-3,5-dione (0.141 g, 0.366 mmol) in dry chloroform (3 ml) is added triethylamine (0.152 ml, 1.09 mmol), and methyl chloroformate (0.084 ml, 1.09 mmol) and the mixture is stirred at room temperature for 2 hours. Solvents are removed, and the residue is purified directly by column chromatography (hexane/ethyl acetate 5:1 ratio) to afford carbonic acid 4-(4′-chloro-4-ethylbiphenyl-3-yl)-2,2,6,6-tetramethyl-5-oxo-5,6-dihydro-2H-pyran-3-yl ester methyl ester (0.150 g) as a white solid.

Workup

  1. customSolvents are removed
  2. customthe residue is purified directly by column chromatography (hexane/ethyl acetate 5:1 ratio)

Sources & evidence

ORD record
ord-ba5bb39725d74f279c0bc50c659b5b69
Source dataset
uspto-grants-2014_03
Patent number
US08680012B2

Reaction notes

Loading…