Ethenone, dichloro- → HCID 13924057, compound

HRID 1960177Notes

Reaction equation

HRID 1960177 reaction equation
[CH2:1]([O:3][CH:4]([CH2:18][CH3:19])[CH2:5][CH2:6][CH2:7][CH2:8][CH:9]1[CH2:16][CH2:15][CH:14]2[CH:10]1CC(=O)C2)[CH3:2].COCCCCCCCC1(C2CCCCCCC2)CCCCCCC1=O.[CH2:46]([O:48][CH:49]([CH2:59][CH3:60])[CH2:50][CH2:51][CH2:52][CH2:53][CH:54]1[CH2:58][CH2:57][CH:56]=[CH:55]1)[CH3:47].[Cl:61][C:62]([Cl:65])=[C:63]=[O:64]>>[Cl:61][C:62]1([Cl:65])[CH:56]2[CH:55]([CH:54]([CH2:53][CH2:52][CH2:51][CH2:50][CH:49]([O:48][CH2:46][CH3:47])[CH2:59][CH3:60])[CH2:58][CH2:57]2)[C:63]1=[O:64].[Cl:61][C:62]1([Cl:65])[C:63](=[O:64])[CH:15]2[CH:16]1[CH:9]([CH2:8][CH2:7][CH2:6][CH2:5][CH:4]([O:3][CH2:1][CH3:2])[CH2:18][CH3:19])[CH2:10][CH2:14]2

Participants

6

Reactant 4

HCID 78338Ethenone, dichloro-HCID 104007392(1H)-Pentalenone, 4-(5-ethoxyheptyl)hexahydro-HCID 13924082HCID 13924082, compound2×HCID 131730366HCID 131730366, compound

Product 2

HCID 13924057HCID 13924057, compoundHCID 13924060HCID 13924060, compound

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

  1. customa method of synthesizing a compound

Sources & evidence

ORD record
ord-f704d940ab8942d8bd3670057c9f1959
Source dataset
uspto-grants-2013_04
Patent number
US08410314B1

Reaction notes

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