p-Toluenesulfonic acid → HCID 22801853, compound

HRID 1154394Notes

Reaction equation

HRID 1154394 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-f639e609b34f4a9b89740f935771e1b5
Source dataset
uspto-grants-1984_12
Patent number
US04489092

Reaction notes

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