Sodium Methoxide → HCID 21502425, compound

HRID 1287305Notes

Reaction equation

HRID 1287305 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH:8]1[CH2:13][CH:12]2[CH:10]([CH:11]2[C:14]([O:16][CH2:17]C)=[O:15])[CH2:9]1.C[O-].[Na+]>CO>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH:8]1[CH2:13][CH:12]2[CH:10]([CH:11]2[C:14]([O:16][CH3:17])=[O:15])[CH2:9]1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 21502421HCID 21502421, compound

Product 1

HCID 21502425HCID 21502425, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Gas-liquid chromatographic analysis of the ethyl 3-[(tetrahydropyran-2-yl)oxy]bicyclo[3.1.0]hexane-6-carboxylate (VIII) obtained as above shows that the product is a mixture of exo and endo isomers in a 4:1 ratio. A solution of 2.8 g. of the above mixture of isomers and 150 mg. of sodium methoxide in 50 ml. of methanol is heated under reflux for 4 hrs. The mixture then is evaporated, the residue extracted with diethyl ether, and the diethyl ether extract evaporated to give the exo isomer of methyl 3-[(tetrahydropyran-2-yl)oxy]bicyclo[ 3.1.0]-hexane-6-carboxylate as an oil; b.p. 130°-133° at 1.1 mm.; homogenous as to the exo isomer by gas-liquid chromatographic analysis and by thin layer chromatographic analysis (silica, developed with benzene-ether 5:1).

Workup

  1. additiona mixture of exo and endo isomers in a 4:1 ratio
  2. additionof the above mixture of isomers and 150 mg
  3. temperatureunder reflux for 4 hrs
  4. customThe mixture then is evaporated
  5. extractionthe residue extracted with diethyl ether
  6. extractionthe diethyl ether extract
  7. customevaporated

Sources & evidence

ORD record
ord-7e70f5eeef3447568cecb2f566137298
Source dataset
uspto-grants-1976_10
Patent number
US03984420

Reaction notes

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