Pyridine → HCID 69199532, compound

HRID 132775Notes

Reaction equation

HRID 132775 reaction equation
[CH3:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][C:7]2([C:13]([O:15][CH2:16]C)=[O:14])[CH2:11][CH2:10][CH2:9][CH:8]2[OH:12])=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:26](Cl)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(Cl)Cl>[CH3:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][C:7]2([C:13]([O:15][CH3:16])=[O:14])[CH2:11][CH2:10][CH2:9][CH:8]2[O:12][C:26](=[O:33])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 69198279HCID 69198279, compound

Product 1

HCID 69199532HCID 69199532, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.24 grams of 2-p-methylbenzyl-2-ethoxycarbonyl-cyclopentanol obtained in Example 18 were diluted with 60 ml of methylene chloride. At room temperature and with magnetic stirring, 2.44 ml of pyridine was slowly added, then 3.55 ml of benzoyl chloride was dropwise added. Upon the completion of the addition, the reaction was continued under reflux condition for 12 hours. Then the procedure as described in Example 23 was followed, to give 7.41 g of yellow liquid. MS: m/e 367(M++1), 366(M+), 293(M+—CO2CH2CH3), 261(M+—C6H5CO2), 216, 198, 170, 155, 105, 91, 77.

Workup

  1. additionUpon the completion of the addition
  2. temperatureunder reflux condition for 12 hours

Sources & evidence

ORD record
ord-1beffa53294b4b3dba14c49c73b25854
Source dataset
uspto-grants-2008_06
Patent number
US07388103B2

Reaction notes

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