Sulfuric Acid → (1S,5R,6S,7R)-6-Formyl-7-methyl-2-oxabicyclo[3,3,0]octan-3-one

HRID 225379

Reaction equation

HRID 225379 reaction equation
C(Cl)Cl.O=[Cr](=O)=O.[CH:8]1[CH:13]=[CH:12][CH:11]=[CH:10]N=1.C1C=[CH:18][CH:17]=[CH:16]N=1.[C:20](=[O:23])(O)[O-].[Na+].S(=O)(=O)(O)[OH:26].[Cl-].[Na+].[OH2:32]>CCOCC>[CH:10]([C@H:11]1[C@H:17]([CH3:18])[CH2:16][C@H:20]2[C@@H:12]1[CH2:13][C:8](=[O:26])[O:23]2)=[O:32]

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 6344Dichloromethane2×HCID 88565Trioxobis(pyridine)chromiumHCID 516892Sodium BicarbonateHCID 57417360Sodium chloride; water

Product 1

HCID 22805158(1S,5R,6S,7R)-6-Formyl-7-methyl-2-oxabicyclo[3,3,0]octan-3-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

At 5°, a solution of 15 g. of the compound prepared according to Example 1(c) in 500 ml. of absolute methylene chloride is added to a solution of 136 g. of freshly prepared Collins reagent in 1 l. of absolute methylene chloride. The mixture is agitated for 30 minutes, combined with 2.5 l. of ether, and shaken in succession four times with respectively 150 ml. of 4% sodium bicarbonate solution, twice with respectively 175 ml. of 10% sulfuric acid, and four times with respectively 150 ml. of brine. After drying over magnesium sulfate, the mixture is evaporated under vacuum, thus obtaining 11.2 g. of the title compound as a brown oil.

Workup

  1. customAt 5°
  2. customof the compound prepared
  3. dry with materialAfter drying over magnesium sulfate
  4. customthe mixture is evaporated under vacuum
  5. customthus obtaining 11.2 g

Sources & evidence

ORD record
ord-64a8397d46c6422585ae73d45ce9ff4a
Source dataset
uspto-grants-1980_11
Patent number
US04235930

Linked notes

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