Ethyl Acetate → HCID 19710589, compound

HRID 726201Notes

Reaction equation

HRID 726201 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]([CH2:7][CH2:8]3)[C:5]=2[C:4]=1[OH:15].CCOC(C)=O>O.C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[C:4](=[O:15])[C:5]2[CH:6]3[CH2:14][CH:9]([C:10]=2[C:11](=[O:13])[CH:12]=1)[CH2:8][CH2:7]3

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 19710533HCID 19710533, compound

Product 1

HCID 19710589HCID 19710589, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

To a vigorously stirred solution of NaIO4 (1.69 g, 7.89 mmol, Baker) in water (50 mL), there was added a solution of 1,2,3,4-tetrahydro-6-methoxy-1,4-methanonaphthalene-5,8-diol (52, 543 mg, 2.63 mmol) in CHCl3 (20 mL). The vigorously stirred reaction immediately became orange. The reaction was allowed to stir for 15 min at rt at which point TLC analysis (10% EtOAc, 90% CHCl3) showed the total consumption of the organic starting material and the formation of a yellow, higher Rf spot. The layers were separated and the aqueous portion extracted with CHCl3 (2×20 mL). The combined organic portion was washed with half saturated brine (30 mL), filtered through cotton and the solvent removed in vacuo. The residue was filtered through a plug of silica gel with CHCl3 elution. Solvent removal gave 53 as a yellow semisolid. Scraping this semisolid with a spatula resulted in a yellow powder. This was further dried in vacuo (470 mg, 88%, pure by TLC and 1H NMR); mp 106°-108° C.; 1H NMR (CDCl3) δ1.16 (m, 2H), 1.40 (d, J=9.0 Hz, 1H), 1.63 (d, J=8.7 Hz, 1H), 1.91 (m, 2H), 3.50 (m, 2H), 3.78 (s, 3H), 5.72 (s, 1H).

Workup

  1. customThe vigorously stirred reaction immediately became orange
  2. customthe total consumption of the
  3. customThe layers were separated
  4. extractionthe aqueous portion extracted with CHCl3 (2×20 mL)
  5. washThe combined organic portion was washed with half saturated brine (30 mL)
  6. filtrationfiltered through cotton
  7. customthe solvent removed in vacuo
  8. filtrationThe residue was filtered through a plug of silica gel with CHCl3 elution
  9. customSolvent removal

Sources & evidence

ORD record
ord-0a2775cd8a42423ca42a1421a8ff5f7d
Source dataset
uspto-grants-1998_01
Patent number
US05708168

Reaction notes

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