p-Toluenesulfonic acid → HCID 70490786, compound

HRID 637323Notes

Reaction equation

HRID 637323 reaction equation
[CH3:1][C:2]1([CH3:18])[C@@H:4]([C:5](O)=[C:6]([S:12][CH3:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])[C@H:3]1[C:15]([OH:17])=[O:16].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:1][C:2]1([CH3:18])[CH:3]2[CH:4]1[CH:5]([CH:6]([S:12][CH3:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])[O:16][C:15]2=[O:17]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 70492638HCID 70492638, compound

Product 1

HCID 70490786HCID 70490786, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 9.67 g of the product of Step A, 80 mg of p-toluene sulfonic acid and 120 ml of benzene was refluxed and 60 ml of benzene were distilled over 90 minutes equipped with a flask of Dean Stark apparatus containing silica gel. The mixture was evaporated to dryness under reduced pressure and the residue was chromatographed over silica gel. Elution with a 6-4 hexane-ethyl acetate mixture yielded 7.36 of 6,6-dimethyl-4-[methylthio-ethoxycarbonyl-methyl]-3-oxa-bicyclo [3,1,0]-hexane-2-one.

Workup

  1. temperaturewas refluxed
  2. distillation60 ml of benzene were distilled over 90 minutes
  3. customequipped with a flask of Dean Stark apparatus
  4. additioncontaining silica gel
  5. customThe mixture was evaporated to dryness under reduced pressure
  6. customthe residue was chromatographed over silica gel
  7. washElution with a 6-4 hexane-ethyl acetate mixture

Sources & evidence

ORD record
ord-fb5ad1d7f80f453c9cfd2dc2ec9b7b09
Source dataset
uspto-grants-1985_12
Patent number
US04556666

Reaction notes

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