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

HRID 1789537Notes

Reaction equation

HRID 1789537 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 9550Diazomethane2×HCID 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 diazomethane 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-463df9a7378c4be6b53eb256f879c341
Source dataset
uspto-grants-1987_08
Patent number
US04689345

Reaction notes

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