Boron trifluoride etherate → Nabilone

HRID 867129Notes

Reaction equation

HRID 867129 reaction equation
[CH3:1][C:2]1([CH3:17])[CH:7]2[CH2:8][CH:3]1[CH:4]=[CH:5][C:6]2(OC(=O)C)[O:9]C(=O)C.[CH3:18][C:19]([C:27]1[CH:28]=[C:29]([OH:34])[CH:30]=[C:31]([CH:33]=1)[OH:32])([CH3:26])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].B(F)(F)F.CCOCC>>[OH:34][C:29]1[C:30]2[C@@H:4]3[CH2:5][C:6](=[O:9])[CH2:7][CH2:8][C@H:3]3[C:2]([CH3:17])([CH3:1])[O:32][C:31]=2[CH:33]=[C:27]([C:19]([CH3:18])([CH3:26])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:28]=1

Participants

4

Reactant 3

HCID 8000Boron trifluoride etherateHCID 918705-(1,1-Dimethylheptyl)resorcinolHCID 20333900HCID 20333900, compound

Product 1

HCID 5284592Nabilone

Procedure

Following the same procedure as set forth above, (+)-6,6-dimethyl-2,2-diacetoxy-3-norpinene was reacted with 5-(1,1-dimethylheptyl)resorcinol in the presence of boron trifluoride diethyl etherate to afford (-)-trans-1-hydroxy-3-(1,1-dimethylheptyl)-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]pyran-9-one.

Sources & evidence

ORD record
ord-0da700afadcd44a0808bc59e2685c876
Source dataset
uspto-grants-1978_07
Patent number
US04102902

Reaction notes

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