HCID 14350667, compound → HCID 14350668, compound

HRID 2291537Notes

Reaction equation

HRID 2291537 reaction equation
[Cl:1][C:2]1[C:14]([Cl:15])=[C:13]([O:16][CH3:17])[CH:12]=[C:11]2[C:3]=1[C:4]1[C:9]([CH2:19][CH2:20][CH3:21])([CH:10]2[OH:18])[CH2:8][CH2:7][C:6](=[O:22])[CH:5]=1.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O.CCOCC.O>[Cl:1][C:2]1[C:14]([Cl:15])=[C:13]([O:16][CH3:17])[CH:12]=[C:11]2[C:3]=1[C:4]1[C:9]([CH2:19][CH2:20][CH3:21])([C:10]2=[O:18])[CH2:8][CH2:7][C:6](=[O:22])[CH:5]=1

Participants

6

Reactant 2

HCID 14350667HCID 14350667, compoundHCID 131709961Jones' reagent

Product 1

HCID 14350668HCID 14350668, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
5 °C

Procedure

To a solution of 5,6-dichloro-9-hydroxy-7-methoxy-9a-propyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (3.03 g, 0.089 mol) in a mixture of acetone (75 ml), ether (75 ml) and water (7 ml) cooled to 5° C. was added Jones reagent (3.4 ml, 2.67N). The reaction mixture was stirred for 1/2 hour at 5° C. then for 11/2 hours at 25° C. The reaction mixture was diluted with ether and H2O, the ether layer washed with NaHCO3, dried over MgSO4, evaporated and chromatographed on silica gel eluting with ethyl acetate-hexane (1:1.5) to give 5,6-dichloro-7-methoxy-9a-propyl-1,2,9,9a-tetrahydro-3H-fluoren-3,9-dione which melts at 167°-9° C.

Workup

  1. custom2 hours
  2. customat 25° C
  3. washthe ether layer washed with NaHCO3
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customchromatographed on silica gel eluting with ethyl acetate-hexane (1:1.5)

Sources & evidence

ORD record
ord-e63051a297e84089972a785b115448a9
Source dataset
uspto-grants-1989_01
Patent number
US04797391

Reaction notes

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