Sodium Bicarbonate → (1R,4aS,6R,8aS)-8a,9,9-Trimethyl-1,2,4a,5,6,7,8,8a-octahydro-1,6-methanonaphthalen-1-ol
반응식
O=[C:2]1[CH2:11][CH2:10][C:9]2([OH:12])[C:4]3([CH3:16])[CH2:5][CH2:6][CH:7]([CH2:15][CH:3]13)[C:8]2([CH3:14])[CH3:13].C([O-])(O)=O.[Na+]>C(O)(=O)C>[CH3:13][C:8]1([CH3:14])[C:9]2([OH:12])[CH2:10][CH:11]=[CH:2][CH:3]3[CH2:15][CH:7]1[CH2:6][CH2:5][C:4]23[CH3:16]참가 물질
4
반응 조건
- 온도
- 25 °C
실험 절차
9.3 mg of N-toluenesulphonylhydrazide was added to a solution of 11.1 mg of 1,2,3,4,4a,5,6,7,8,8a-decahydro-2-oxo-4a-hydroxy-5,5,8a-trimethyl-1,6-methanonaphthalene in hot acetic acid. The mixture was refluxed for 10 minutes, subsequently poured into saturated aqueous NaHCO3 solution, extracted with CH2Cl2 and evaporated. The solution of the residue in 4 ml of ether was treated slowly at 25° C. with a 1-N solution of methyllithium in ether (0.225 ml), then stirred at 25° C. under argon, then poured into water and extracted with CH2Cl2. Chromatography (SiO2 /CH2Cl2) and sublimation at 100°-120° C. gave (+)-norpatchoulenol (m.p. 135°-141° C., 6.8 mg, 68% yield).