Oxalyl chloride → HCID 58611843, compound

HRID 2375213Notes

Reaction equation

HRID 2375213 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2([C:17]([OH:19])=O)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:7][CH:6]=1)=[O:4].C(Cl)(=O)C([Cl:23])=O>ClCCl.CN(C)C=O>[Cl:23][C:17]([C:11]1([C:8]2[CH:9]=[CH:10][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:19]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 58611869HCID 58611869, compound

Product 1

HCID 58611843HCID 58611843, compoundYield 100.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 1-[4-(methoxycarbonyl)phenyl]-cyclohexanecarboxylic acid (E14) (0.174 g, 0.66 mmol) in dry dichloromethane (4 ml) under argon atmosphere at ice bath temperature oxalyl chloride (0.648 g, 5.10 mmol) and one drop of dimethylformamide were added. The reaction mixture was stirred at room temperature for 15 minutes and at 40° C. for one hour, then concentrated under reduced pressure to give crude title compound (0.187 g, ca. 100%). The crude product was immediately utilized in the next step of the synthesis without further purification.

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d7ed545c1f1a4caa913d55dcc90d735d
Source dataset
uspto-grants-2008_12
Patent number
US07465719B2

Reaction notes

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