Chloroform → HCID 19710581, compound

HRID 726199Notes

Reaction equation

HRID 726199 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>O>[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)[CH:8]=[CH:7]3

Participants

5

Reactant 3

HCID 6212ChloroformHCID 8857Ethyl AcetateHCID 19710530HCID 19710530, compound

Product 1

HCID 19710581HCID 19710581, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a vigorously stirred solution of NaIO4 (471 mg, 2.20 mmol; Baker) in water (15 mL), there was added solid 1,4-dihydro-6-methoxy-1,4-methanonaphthalene-5,8-diol (48, 150 mg, 734 μmol) in one portion. The reaction immediately became orange and a precipitate formed. The reaction was allowed to stir at rt for 15 min at which point TLC analysis (10% EtOAc, 90% CHCl3) indicated total consumption of 48. The reaction mixture was extracted with CHCl3 (3×15 mL). The extract was washed with half saturated brine (1×25 mL), filtered through cotton and the solvent removed in vacuo to yield a gummy yellow solid. This was triturated with hexanes (2 mL) and dried in vacuo to yield 49 as a yellow powder (134 mg, 90%, pure by TLC and 1H NMR); mp 117°-118° C.; 1H NMR (CDCl3) δ2.26 (d, J=7.2 Hz, 1H), 2.33 (d, J=6.9 Hz, 1H), 3.79 (s, 3H), 4.10 (m, 2H), 5.70 (s, 1H), 6.86 (m, 2H). Note: this material decomposes if stored for extended periods at rt.

Workup

  1. customThe reaction immediately became orange
  2. customa precipitate formed
  3. customconsumption of 48
  4. extractionThe reaction mixture was extracted with CHCl3 (3×15 mL)
  5. washThe extract was washed with half saturated brine (1×25 mL)
  6. filtrationfiltered through cotton
  7. customthe solvent removed in vacuo
  8. customto yield a gummy yellow solid
  9. customThis was triturated with hexanes (2 mL)
  10. customdried in vacuo

Sources & evidence

ORD record
ord-752a6837a9c1452d98c15c450fdfb94d
Source dataset
uspto-grants-1998_01
Patent number
US05708168

Reaction notes

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