Lithium iodide → 2(1H)-Pentalenone, 4-(5-ethoxyheptyl)hexahydro-
Reaction equation
[I-].C[S+](C)C.[CH2:6]([O:8][CH:9]([CH2:23][CH3:24])[CH2:10][CH2:11][CH2:12][CH2:13][CH:14]1[CH2:22][CH2:21][CH:20]2[CH:15]1[CH2:16][C:17]12[CH2:19][O:18]1)[CH3:7].[I-].[Li+]>>[CH2:6]([O:8][CH:9]([CH2:23][CH3:24])[CH2:10][CH2:11][CH2:12][CH2:13][CH:14]1[CH2:22][CH2:21][CH:20]2[CH:15]1[CH2:16][C:19](=[O:18])[CH2:17]2)[CH3:7]Participants
Procedure
Disclosed is a method of synthesizing a compound, such as 6-(5-ethoxyhept-1-yl)bicyclo[3.3.0]octan-3-one or methoxyheptyl bicyclooctanone, from 3-(5-ethoxyhept-1-yl)cyclopentene or other starting material. Such a method comprises reacting 3-(5-ethoxyhept-1-yl)cyclopentene with dichloroketene to form a first mixture comprising 7,7-dichloro-4-(5-ethoxyhept-1-yl)bicyclo[3.2.0]heptan-6-one and 6,6-dichloro-4-(5-ethoxyhept-1-yl)bicyclo[3.2.0]-heptan-7-one. The first mixture is reacted with acetic acid and zinc to form a second mixture comprising 4-(5-ethoxyhept-1-yl)bicyclo[3.2.0]heptan-6-one and 4-(5-ethoxyhept-1-yl)bicyclo-[3.2.0]heptan-7-one. The second mixture is reacted with trimethylsulfonium iodide to form a third mixture comprising 2-(5-ethoxyhept-1-yl)spiro[bicyclo[3.2.0]heptane-6,2′-oxirane]. The third mixture is reacted with lithium iodide to form 6-(5-ethoxyhept-1-yl)bicyclo[3.3.0]octan-3-one.
Workup
- customto form a third mixture
Sources & evidence
- ORD record
- ord-26b42c377a7a468eb39adb0cf2c9d516
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08410314B1
Reaction notes
Loading…