HCID 15125154, compound → HCID 15125155, compound

HRID 373386Notes

Reaction equation

HRID 373386 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:18]2[C:27]3[CH2:26][CH2:25][CH2:24][CH2:23][C:22]=3[C:21]([CH3:28])=[C:20]([CH3:29])[C:19]=2[O:30][CH3:31])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:4][CH:3]=1.[Cr](Cl)([O-])(=O)=[O:33].[NH+]1C=CC=CC=1>C1C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:18]2[C:19]([O:30][CH3:31])=[C:20]([CH3:29])[C:21]([CH3:28])=[C:22]3[C:27]=2[CH2:26][CH2:25][CH2:24][C:23]3=[O:33])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 15125154HCID 15125154, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 15125155HCID 15125155, compoundYield 53.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of methyl 7-(4-fluorophenyl)-7-(2-methoxy-3,4-dimethyl-5,6,7,8-tetrahydronaphthyl)heptanoate (0.4 g) in benzene (12 ml) was added a mixture of pyridinium chlorochromate (1 g) and cerite (1.8 g) and the mixture was refluxed for 5 hours. After cooling, insoluble materials were filtered off and the filtrate was washed with water and saturated saline and dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was subjected to silica gel column chromatography to obtain methyl 7-(4-fluorophenyl)-7-(6-methoxy-7,8-dimethyl-1-oxo-1,2,3,4-tetrahydro-5naphthyl)-heptanoate (0.22 g) (Compound 59). The physical properties and spectrum data thereof are shown in Tables 3 and 4.

Workup

  1. temperaturethe mixture was refluxed for 5 hours
  2. temperatureAfter cooling
  3. filtrationinsoluble materials were filtered off
  4. washthe filtrate was washed with water and saturated saline
  5. dry with materialdried with anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-88f4879806ab4c6bb2abafcc99e9d7f1
Source dataset
uspto-grants-1992_11
Patent number
US05162571

Reaction notes

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