Dichloromethane → HCID 69198815, compound

HRID 132787Notes

Reaction equation

HRID 132787 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][CH2:4][C:3]1([CH2:12][CH2:13][CH3:14])[C:7]([O:9][CH2:10][CH3:11])=[O:8].C(Cl)Cl.[CH3:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1>N1C=CC=CC=1>[CH2:12]([C:3]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:4][CH2:5][CH2:6][CH:2]1[O:1][C:23](=[O:24])[C:22]1[CH:26]=[CH:27][C:19]([CH3:18])=[CH:20][CH:21]=1)[CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 134054-Methylbenzoyl ChlorideHCID 69199039HCID 69199039, compound

Product 1

HCID 69198815HCID 69198815, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Ethyl 2-hydroxy-1-n-propyl-cyclopentane carboxylate (6.00 g) was diluted using 60 ml of methylene chloride. At room temperature and with magnetic stirring, pyridine (3.66 ml) was slowly added, then 4-methyl-benzoyl chloride (6.12 ml) was dropwise added. Upon the completion of the addition, the reaction was continued for 12 hours. Then solvent was removed, and the residue was extracted using ethyl acetate and water. Organic layer was washed, in turn, using 10% hydrochloric acid aqueous solution to pH of about 2, using saline solution to neutrality, using 10% aqueous solution of sodium carbonate for three times, and then using saline solution to neutrality. The organic layer was dried, and removing solvent gave 10.41 g of yellow liquid. MS: m/e 319(M+′+1), 318(M+′), 317(M+′−1), 259, 230, 199, 182, 153, 105(base), 77.

Workup

  1. additionUpon the completion of the addition
  2. customThen solvent was removed
  3. extractionthe residue was extracted
  4. washOrganic layer was washed, in turn
  5. customThe organic layer was dried
  6. customremoving solvent

Sources & evidence

ORD record
ord-926f87cbae0845059fa7b6f9c25f036b
Source dataset
uspto-grants-2008_06
Patent number
US07388103B2

Reaction notes

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