Dichloromethane → HCID 69198959, compound

HRID 132788Notes

Reaction equation

HRID 132788 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][CH2:4][C:3]1([CH2:12][CH2:13][CH2:14][CH3:15])[C:7]([O:9][CH2:10][CH3:11])=[O:8].C(Cl)Cl.[CH3:19][C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=1)[C:23](Cl)=[O:24]>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][CH:28]=[C:20]([CH3:19])[CH:21]=1)[CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 743753-Methylbenzoyl chlorideHCID 69199000HCID 69199000, compound

Product 1

HCID 69198959HCID 69198959, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Ethyl 2-hydroxy-1-n-butyl-cyclopentane carboxylate (6.42 g) was diluted using 60 ml of methylene chloride. At room temperature and with magnetic stirring, pyridine (3.66 ml) was slowly added, then 3-methyl-benzoyl chloride (6.00 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, and then using 10% aqueous solution of sodium carbonate for three times, then using saline solution to neutrality. The organic layer was dried, and removing solvent gave 11.99 g of brown liquid. MS: m/e 332(M+′), 287, 213, 196, 167, 119(base), 99.

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-26c5e6f2402c4090a230bd21ac79da9a
Source dataset
uspto-grants-2008_06
Patent number
US07388103B2

Reaction notes

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