p-Toluenesulfonic acid → HCID 22801853, compound

HRID 894640Notes

Reaction equation

HRID 894640 reaction equation
[CH:1]([C@H:3]1[C@H:10]([O:11][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:9][C@H:8]2[C@@H:4]1[CH2:5][C:6](=[O:20])[O:7]2)=[O:2].C([O-])([O-])[O:22][CH2:23][CH3:24].[C:27]1(C)C=CC(S(O)(=O)=O)=C[CH:28]=1.C(=O)(O)[O-].[Na+]>CCOCC.O.C(O)C.C(COC)OC>[CH2:27]([O:2][CH:1]([O:22][CH2:23][CH3:24])[C@H:3]1[C@H:10]([O:11][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:9][C@H:8]2[C@@H:4]1[CH2:5][C:6](=[O:20])[O:7]2)[CH3:28]

Participants

9

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 11000244(3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoateHCID 53630039Ethylorthoformate

Product 1

HCID 22801853HCID 22801853, compound

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

7.7 g. of (1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3,3,0]octan-3-one was dissolved in 80 ml. of absolute dimethoxyethane, combined with 13.29 g. of ethyl orthoformate in 30 ml. of absolute ethanol and 120 mg. of p-toluenesulfonic acid and stirred overnight at room temperature under argon. Thereafter, the reaction mixture was diluted with ether and shaken in succession three times with 100 ml. of sodium bicarbonate solution as well as 100 ml. of water. The organic phase was dried over sodium sulfate and concentrated to dryness, thus obtaining 8.55 g. of the desired compound.

Workup

  1. dry with materialThe organic phase was dried over sodium sulfate
  2. concentrationconcentrated to dryness
  3. customthus obtaining 8.55 g

Sources & evidence

ORD record
ord-e2d58fffec164bfa913e1a00d9d39dd1
Source dataset
uspto-grants-1981_08
Patent number
US04284646

Reaction notes

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