Process for preparing 6-isopropenyl-3-methyl-9-decenyl acetate, and intermediates therefor

A process for preparing 6-isopropenyl-3-methyl-9-decenyl acetate of the following formula (5):

• wherein Ac represents an acetyl group,
• the process comprising steps of:
• subjecting a 2-methyl-2,6-heptadiene compound of the following general formula (1) having a leaving group X at position 1:
• wherein X represents an acyloxy group having 1 to 10 carbon atoms including the carbon atom of the carbonyl group, an alkanesulfonyloxy group having 1 to 10 carbon atoms, an arenesulfonyloxy group having 6 to 20 carbon atoms, or a halogen atom, to a nucleophilic substitution reaction with a 3-methylpentyl nucleophilic reagent of the following general formula (2) having a protected hydroxyl group at position 5:
• wherein M represents Li, MgZ1, ZnZ1, Cu, CuZ1, or CuLiZ1, wherein Z1 represents a halogen atom or a CH2CH2CH(CH3)CH2CH2OR group, and R represents a protecting group for a hydroxyl group,
• to form a 6-isopropenyl-3-methyl-9-decene compound of the following general formula (3) having a protected hydroxyl group at position 1:
• wherein R is as defined above;
• subjecting the 6-isopropenyl-3-methyl-9-decene compound (3) having the protected hydroxyl group at position 1 to a deprotection reaction to form 6-isopropenyl-3-methyl-9-decenol of the following formula (4):
• and
• acetylating 6-isopropenyl-3-methyl-9-decenol (4) to form 6-isopropenyl-3-methyl-9-decenyl acetate (5).