Diazomethane → HCID 15053006, compound

HRID 1789539Notes

Reaction equation

HRID 1789539 reaction equation
ClCCCCC(OCC)CC.[CH2:12]([O:14][CH:15]([CH2:25][CH3:26])[CH2:16][CH2:17][CH2:18][CH2:19][CH:20]1[CH2:24][CH2:23][CH:22]=[CH:21]1)[CH3:13].[Cl:27][C:28]1([Cl:46])[C:34](=[O:35])[CH:33]2C1CCC2CCCCC(OCC)CC.[N+](=C)=[N-]>>[Cl:27][C:28]1([Cl:46])[C:34](=[O:35])[CH2:33][CH:24]2[CH:23]1[CH2:22][CH2:21][CH:20]2[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]([O:14][CH2:12][CH3:13])[CH2:25][CH3:26]

Participants

5

Reactant 4

HCID 9550DiazomethaneHCID 13924057HCID 13924057, compound2×HCID 139240811-Chloro-5-ethoxyheptaneHCID 13924082HCID 13924082, compound

Product 1

HCID 15053006HCID 15053006, compound

Procedure

The corresponding 2-(5-ethoxyhept-1-yl) homologs are prepared by substituting an equivalent amount of 1-chloro-5-ethoxyheptane in the Grignard reaction of Example 1 in place of the 5-methoxy homolog and using the reaction sequence shown above to prepare first the 3-(5-ethoxyhept-1-yl)cyclopentene, which is then converted to the 6,6-dichloro-2-(5-ethoxyhept-1-yl)bicyclo[3.2.0]heptan-7-one {7,7-dichloro-4-(5-ethoxyheptyl)bicyclo[3.2.0]heptan-6-one} of this invention. The diazomethane reaction described for the methoxy homolog produces the 6,6-dichloro-2-(5-ethoxyhept-1yl) bicyclo[3.3.0]octan-7-one {7,7-dichloro-4-(5-ethoxyheptyl)bicyclo[3.2.0]heptan-6-one}.

Sources & evidence

ORD record
ord-cc943bb8137844e696e7511318aca43f
Source dataset
uspto-grants-1987_08
Patent number
US04689345

Reaction notes

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