Hydrochloric Acid → HCID 19710530, compound

Participants

Reaction Steps

To stirred MeOH (65 mL), which had been purged with N2 for 5 min, there was added 1,4,4a,8a-tetrahydro-6-methoxy-1,4-methanonaphthalene-5,8-dione (47, 1.50 g, 7.30 mmol) to give a solution. Solid Na2CO3 (2.02 g, 14.6 mmol) was then added under N2. The resulting light green suspension was allowed to stir under N2 for 15 min at rt. TLC analysis (10% MeOH, 90% CHCl3) indicated total consumption of the organic starting material. While still under N2, the reaction was diluted with H2O (20 mL). The pH was adjusted to slightly acidic by the slow and careful addition of concd HCl, after which the solution was light pink. The methanol was then removed in vacuo (vacuum relieved with N2) to give a light green solution. The pH was approximately 8. The pH was then adjusted to 2 with 10% HCl at which point the product crystallized. The crystals were collected, washed with 10% HCl (4×3 mL) and dried in vacuo to yield 48 as a near colorless crystalline solid (1.32 g, 88%, pure by TLC and 1H NMR); mp 151°-153° C.; 1H NMR (vide infra).

Provenance & Evidence