Chloroform → HCID 19710581, compound

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.

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

ORD record

ord-350434b360524e0788238ad2d96ac06b

Source dataset

uspto-grants-1995_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05476933