Diethyl Ether → 1,2,3,4,4a,9b-Hexahydro-1,4a,9b-trimethyl-1,4-methanodibenzofuran

HRID 1941013Notes

Reaction equation

HRID 1941013 reaction equation
Br[C:2]1[CH:7]=CC=[CH:4][C:3]=1OC.[CH2:10]([Li])[CH2:11][CH2:12][CH3:13].C[C@@:16]12[C:22](=[O:23])[C:21]([CH3:25])(C)[CH:19](C1)[CH2:18][CH2:17]2.[Cl-].[NH4+].[CH2:28](OCC)C>>[CH3:13][C:12]12[CH2:7][CH:2]([C:3]3([CH3:4])[C:25]1([CH3:28])[C:21]1[CH:19]=[CH:18][CH:17]=[CH:16][C:22]=1[O:23]3)[CH2:10][CH2:11]2

Participants

6

Reactant 5

HCID 3283Diethyl Ether2×HCID 113582-BromoanisoleHCID 25517Ammonium ChlorideHCID 12049113(1s)-1,3,3-Trimethyl-norbornan-2-oneHCID 178418339Butyllithium

Product 1

HCID 187895091,2,3,4,4a,9b-Hexahydro-1,4a,9b-trimethyl-1,4-methanodibenzofuran

Procedure

50 g (0.267 mol) of bromoanisole, in solution in 120 ml of ethyl ether, were treated at 0° C. with 200 ml of n-butyllithium (1.6M in hexane) and the mixture was maintained under stirring at room temperature overnight. 41.57 g (273 mmol) of (+)-fenchone (Fluka) in 100 ml of ethyl ether were then added dropwise and the mixture was maintained under stirring for 6 h at room temperature. The reaction mixture was poured into 200 ml of a saturated ammonium chloride solution.

Workup

  1. temperaturethe mixture was maintained
  2. temperaturethe mixture was maintained
  3. stirringunder stirring for 6 h at room temperature

Sources & evidence

ORD record
ord-3cc23fe1cf134b1a9840823fd8d29df5
Source dataset
uspto-grants-1997_12
Patent number
US05702710

Reaction notes

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