p-Toluenesulfonic acid → (1S,5R,6S)-6-Diethoxymethyl-2-oxabicyclo-[3,3,0]octan-3-one

HRID 225384Notes

Reaction equation

HRID 225384 reaction equation
C([C@H:3]1[CH2:10][CH2:9][C@H:8]2[C@@H:4]1[CH2:5][C:6](=[O:11])[O:7]2)=O.[CH:12]([O:19][CH2:20][CH3:21])([O:16][CH2:17][CH3:18])OCC.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>CCOCC.O.C(O)C>[CH2:20]([O:19][CH:12]([O:16][CH2:17][CH3:18])[C@H:3]1[CH2:10][CH2:9][C@H:8]2[C@@H:4]1[CH2:5][C:6](=[O:11])[O:7]2)[CH3:21]

Participants

8

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 31214Ethyl orthoformateHCID 516892Sodium BicarbonateHCID 12884327(1S,5R,6S)-6-formyl-2-oxabicyclo[3,3,0]octan-3-one

Product 1

HCID 22813163(1S,5R,6S)-6-Diethoxymethyl-2-oxabicyclo-[3,3,0]octan-3-one

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

4.3 g. of (1S,5R,6S)-6-formyl-2-oxabicyclo-[3,3,0]octan-3-one [see Example 9(a)], 15 ml. of triethyl orthoformate, and 40 mg. of p-toluenesulfonic acid in 15 ml. of absolute ethyl alcohol are agitated for 16 hours at 20° under argon. The mixture is then diluted with ether, shaken in succession with sodium bicarbonate solution and water, dried over magnesium sulfate, and evaporated under vacuum, thus obtaining 4.8 g. of the title compound as an oil which is completely uniform as determined by thin-layer chromatography.

Workup

  1. dry with materialdried over magnesium sulfate
  2. customevaporated under vacuum
  3. customthus obtaining 4.8 g

Sources & evidence

ORD record
ord-37dd50195fec4e079b2d9d0d31cf8d35
Source dataset
uspto-grants-1980_11
Patent number
US04235930

Reaction notes

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