Chloroform → HCID 19710533, compound

HRID 726200Notes

Reaction equation

HRID 726200 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([OH:13])[C:10]2[CH:9]3[CH2:14][CH:6]([CH:7]=[CH:8]3)[C:5]=2[C:4]=1[OH:15].CCOC(C)=O.C(Cl)(Cl)Cl>CO.[Pd]>[CH3:1][O:2][C:3]1[CH:12]=[C:11]([OH:13])[C:10]2[CH:9]3[CH2:14][CH:6]([CH2:7][CH2:8]3)[C:5]=2[C:4]=1[OH:15]

Participants

6

Reactant 3

HCID 6212ChloroformHCID 8857Ethyl AcetateHCID 19710530HCID 19710530, compound

Product 1

HCID 19710533HCID 19710533, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 1,4-dihydro-6-methoxy-1,4-methanonaphthalene-5,8-diol (48, 1.30 g, 6.36 mmol) in MeOH (100 mL) was hydrogenated (Parr hydrogenator, 20 psi) over Pd (10% on C, 100 mg, Aldrich) for 15 min. TLC analysis (10% EtOAc, 90% CHCl3) indicated total consumption of the organic starting material to give a higher Rf product. The catalyst was removed by filtration through celite during which time the filtrate turned light green. Color change was attributed to trace air oxidation of the desired product to the corresponding quinone. After MeOH removal, the residue was filtered through silica gel with CHCl3 elution. Solvent removal yielded 52 as a brown gummy solid, which was found suitable for the next reaction without further purification (1.28 g, 98%, purity >95% by TLC and 1H NMR analyses); 1H NMR (CDCl3) δ1.20 (m, 2H), 1.49 (d, J=8.7 Hz, 1H), 1.70 (m, 1H), 1.88 (m, 2H), 3.42 (s, 1H), 3.62 (s, 1H), 3.80 (s, 3H), 4.37 (s, 1H), 5.17 (s, 1H), 6.19 (s, 1H).

Workup

  1. customfor 15 min
  2. customconsumption of the
  3. customto give a higher Rf product
  4. customThe catalyst was removed by filtration through celite during which time the filtrate
  5. customAfter MeOH removal
  6. filtrationthe residue was filtered through silica gel with CHCl3 elution
  7. customSolvent removal

Sources & evidence

ORD record
ord-202134d8a99d476ea6df27307782425f
Source dataset
uspto-grants-1998_01
Patent number
US05708168

Reaction notes

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