Sodium Chloride → HCID 131717409, compound

HRID 1197066Notes

Reaction equation

HRID 1197066 reaction equation
[OH:1][CH:2]([CH2:26][CH2:27][CH2:28][OH:29])/[CH:3]=[CH:4]/[CH:5]=[C:6]1[C:10](=[O:11])[C:9]([S:12][CH3:13])=[CH:8][C:7]1([OH:25])[CH2:14][CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[C:30](Cl)(=[O:32])[CH3:31].[Cl-].[Na+].[O:36](CCCCC1C(=O)CCC=1)[C:37]1C=CC=C[CH:38]=1>ClCCl.C(N(CC)CC)C>[C:30]([O:1][CH:2]([CH2:26][CH2:27][CH2:28][O:29][C:37](=[O:36])[CH3:38])/[CH:3]=[CH:4]/[CH:5]=[C:6]1[C:10](=[O:11])[C:9]([S:12][CH3:13])=[CH:8][C:7]1([OH:25])[CH2:14][CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:32])[CH3:31]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 6367Acetyl chlorideHCID 21570786HCID 21570786, compoundHCID 86745875HCID 86745875, compound

Product 1

HCID 131717409HCID 131717409, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 23 mg of 5-[(E)-4,7-dihydroxy-2-heptenylidene]-4-hydroxy-2-methylthio-4-(4-phenoxybutyl)-2-cyclopentenone obtained in Example 91 dissolved in 2 ml of dichloromethane was added 200 μl of triethylamine. Under ice-cooling and stirring. 20 μl of acetylchloride was added, and the mixture was stirred at 0° C. for 2 hours. Saturated aqueous sodium chloride was added, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, filtrate and concentrated, followed by silica gel column chromatography to give 11 mg (yield 43%) of 5-[(E)-4,7-diacetoxy-2-heptenylidene]-4-hydroxy-2-methylthio-4-(4-phenoxybutyl)-2-cyclopentenone (J) and 4 mg (yield 17%) of 5-[(E)-4,7-diacetoxy-2-heptenylidene]-4-acetoxy-2-methylthio-4-(4-phenoxybutyl-2-cyclopentenone (K).

Workup

  1. temperatureUnder ice-cooling
  2. stirringthe mixture was stirred at 0° C. for 2 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous sodium sulfate, filtrate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-319c70d042bf4526b96dd0d44b1a2fa2
Source dataset
uspto-grants-1992_05
Patent number
US05116869

Reaction notes

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