Dichloromethane → HCID 69199038, compound

HRID 132773Notes

Reaction equation

HRID 132773 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.C(Cl)Cl.[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>N1C=CC=CC=1>[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:22](=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 7412Benzoyl chlorideHCID 69199018HCID 69199018, compound

Product 1

HCID 69199038HCID 69199038, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

12.4 grams of 2-benzyl-2-ethoxycarbonyl-cyclopentanol obtained from Example 14 were diluted using 60 ml of methylene chloride. At room temperature and with magnetic stirring, 6.108 ml of pyridine was slowly added, then 8.876 ml of benzoyl chloride 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. The organic layer was dried, and removing solvent gave 19.71 g of yellow liquid. MS: m/e 353(M++1), 352(M+), 351(M+−1), 279(M+—CO2CH2CH3), 261(M+—CH2C6H5), 247(M+—C6H5CO), 231(M+—C6H5CO2), 201, 184, 156, 139, 105 (base), 91, 77.

Workup

  1. customThen solvent was removed
  2. extractionthe residue was extracted
  3. washOrganic layer was washed, in turn
  4. customThe organic layer was dried
  5. customremoving solvent

Sources & evidence

ORD record
ord-a7e719d196294abb8dbb3b868b34b2a9
Source dataset
uspto-grants-2008_06
Patent number
US07388103B2

Reaction notes

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