Diazald → 6,6-Dichloro-2-(5-methoxyhept-1-yl)bicyclo[3.3.0]octan-7-one

HRID 1722360Notes

Reaction equation

HRID 1722360 reaction equation
[Cl:1][C:2]1([Cl:19])[C:8](=[O:9])[CH:7]2[CH:3]1[CH2:4][CH2:5][CH:6]2[CH2:10][CH2:11][CH2:12][CH2:13][CH:14]([O:17][CH3:18])[CH2:15][CH3:16].[N+](=[CH2:22])=[N-].CN(N=O)S(C1C=CC(C)=CC=1)(=O)=O.[OH-].[K+]>CCOCC.C(O)C.C(O)(=O)C>[Cl:19][C:2]1([Cl:1])[C:8](=[O:9])[CH2:22][CH:7]2[CH:3]1[CH2:4][CH2:5][CH:6]2[CH2:10][CH2:11][CH2:12][CH2:13][CH:14]([O:17][CH3:18])[CH2:15][CH3:16]

Participants

8

Reactant 4

HCID 6628DiazaldHCID 9550DiazomethaneHCID 14797Potassium HydroxideHCID 139240447,7-Dichloro-4-(5-methoxyheptyl)bicyclo[3.2.0]heptan-6-one2×

Product 1

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

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

The starting material, 6,6-dichloro-2-(5-methoxyhept-1-yl)bicyclo[3.2.0]heptan-7-one {7,7-dichloro-4-(5-methoxyheptyl)bicyclo[3.2.0]heptan-6-one} (5 g), is dissolved in 100 ml of ether and transferred to a 500 ml, round-bottomed flask. An excess of diazomethane is generated in situ by reacting N-methyl-N-nitroso-p-toluene sulfonamide (60 g) with potassium hydroxide in ethanol. The diaxomethane is allowed to react for 50 minutes, after which time acetic acid is added to destroy any remaining diazomethane. The solution is extracted with ether and dried over anhydrous sodium sulfate and yields the crude product as an orange oil.

Workup

  1. customto react for 50 minutes
  2. customto destroy any remaining diazomethane
  3. extractionThe solution is extracted with ether
  4. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-db75f2a0e2804c6a8b3489f971aab304
Source dataset
uspto-grants-1989_08
Patent number
US04855322

Reaction notes

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