Pyridine → HCID 69200428, compound

HRID 132774Notes

Reaction equation

HRID 132774 reaction equation
[CH2:1]([C:8]1([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:12][CH2:11][CH2:10][CH:9]1[OH:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH3:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][CH:27]=1>C(Cl)Cl>[CH2:1]([C:8]1([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:12][CH2:11][CH2:10][CH:9]1[O:13][C:30](=[O:31])[C:29]1[CH:33]=[CH:34][C:26]([CH3:25])=[CH:27][CH:28]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 134054-Methylbenzoyl ChlorideHCID 69199018HCID 69199018, compound

Product 1

HCID 69200428HCID 69200428, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7.44 grams of 2-benzyl-2-ethoxycarbonyl-cyclopentanol obtained in Example 14 were diluted with 60 ml of methylene chloride. At room temperature and with magnetic stirring, 3.66 ml of pyridine was slowly added, then 6.12 ml of 4-methyl 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 12.53 g of yellow liquid. MS: m/e 367(M++1), 366(M+), 364(M+−2), 293(M+—CO2CH2CH3), 247(M+—CH3C6H4CO), 231(M+—CH3C6H4CO2), 201, 184, 156, 139, 119 (base), 91, 77.

Workup

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

Sources & evidence

ORD record
ord-32ae2b18353a43e98e9a6e421004ff19
Source dataset
uspto-grants-2008_06
Patent number
US07388103B2

Reaction notes

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