6,6-Dichloro-2-(5-methoxyhept-1-yl)bicyclo[3.3.0]octan-7-one → Octahydro-4-(5-methoxyheptyl)-2-pentalenol

HRID 1789541Notes

Reaction equation

HRID 1789541 reaction equation
Cl[C:2]1(Cl)[C:9](=[O:10])[CH2:8][CH:7]2[CH:3]1[CH2:4][CH2:5][CH:6]2[CH2:11][CH2:12][CH2:13][CH2:14][CH:15]([O:18][CH3:19])[CH2:16][CH3:17].ClC1(Cl)C(O)CC2C1CCC2CCCCC(OC)CC>C(O)(=O)C.[Zn]>[CH3:19][O:18][CH:15]([CH2:16][CH3:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH:6]1[CH2:5][CH2:4][CH:3]2[CH:7]1[CH2:8][CH:9]([OH:10])[CH2:2]2

Participants

5

Reactant 2

HCID 139240476,6-Dichloro-2-(5-methoxyhept-1-yl)bicyclo[3.3.0]octan-7-oneHCID 200287126,6-Dichloro-2-(5-methoxyhept-1-yl) bicyclo[3.3.0]octan-7-ol

Product 1

HCID 15053012Octahydro-4-(5-methoxyheptyl)-2-pentalenol

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

The reactions of this example can also be conducted using an equivalent amount of 6,6-dichloro-2-(5-methoxyhept-1-yl)bicyclo [3.3.0]octan-7-one {1-1-dichlorohexahydro-4-(5-methoxyheptyl)-2 (1H)-pentalenone} to first prepare 6,6-dichloro-2-(5-methoxyhept-1-yl) bicyclo[3.3.0]octan-7-ol {1,1-dichlorooctahydro-4-(5-methoxyheptyl)-2-pentalenol} which is then treated by the zinc in glacial acetic acid to produce 2-(5-methoxyhept-1-yl)bicyclo [3.3.0]-octan-7-ol {octahydro-4-(5-methoxyheptyl)-2-pentalenol}.

Sources & evidence

ORD record
ord-bed3dee93a03496f83549f0ad35d1929
Source dataset
uspto-grants-1987_08
Patent number
US04689345

Reaction notes

Loading…