Diethyl Ether → Ethyl 2-(oxan-2-yloxy)cyclopropane-1-carboxylate

HRID 496049

Reaction equation

HRID 496049 reaction equation
[CH:1]([O:3][CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][O:5]1)=[CH2:2].[N+](=C[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N-].[CH3:18]COCC>C([O-])(=O)C.[Rh+3].C([O-])(=O)C.C([O-])(=O)C>[O:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH:4]1[O:3][CH:1]1[CH2:18][CH:2]1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

5

Reactant 3

HCID 3283Diethyl Ether2×HCID 12192Ethyl diazoacetateHCID 115283452-Vinyloxytetrahydropyran

Product 1

HCID 22325102Ethyl 2-(oxan-2-yloxy)cyclopropane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 168478Rhodium acetateCatalyst

Procedure

To a solution of 0.75 mol of the compound obtained in Step 1 in 200 ml of ether there are added 1.5 g of rhodium acetate and then, over 6 hours, a solution of 93 g of ethyl diazoacetate in 50 ml of ether. After stirring at ambient temperature for 16 hours, the reaction mixture is filtered and is then distilled at 50-90° C. and 0.5 torr. The residue obtained is redistilled at 80-84° C. and 0.2 torr, allowing the expected product to be isolated.

Workup

  1. filtrationthe reaction mixture is filtered
  2. distillationis then distilled at 50-90° C.
  3. customThe residue obtained
  4. distillationis redistilled at 80-84° C.
  5. customto be isolated

Sources & evidence

ORD record
ord-9fce2bd7ace74964974f6ee128712839
Source dataset
uspto-grants-2005_09
Patent number
US06943184B2

Linked notes

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