p-Toluenesulfonic acid → (1R,4R,5S) 4-[dihydro-2-oxo-3-(2H)-thienyl]-6,6-dimethyl-3-oxabicyclo-(3,1,0)-hexan-2-one

HRID 648366Notes

Reaction equation

HRID 648366 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:12]=[C:13]1[CH:17]([CH:18]([OH:27])[C@H:19]2[C@@H:21]([C:22]([OH:24])=O)[C:20]2([CH3:26])[CH3:25])[CH2:16][CH2:15][S:14]1>C1C=CC=CC=1>[O:12]=[C:13]1[CH:17]([C@H:18]2[C@H:19]3[C@H:21]([C:20]3([CH3:25])[CH3:26])[C:22](=[O:24])[O:27]2)[CH2:16][CH2:15][S:14]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 70534022(1R,3S) 3[(dihydro-2-oxo-3(2H)-thienyl)-hydroxymethyl]-2,2-dimethyl-cyclopropane-1-carboxylic acid

Product 1

HCID 22824566(1R,4R,5S) 4-[dihydro-2-oxo-3-(2H)-thienyl]-6,6-dimethyl-3-oxabicyclo-(3,1,0)-hexan-2-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

50 mg of p-toluene sulfonic acid were added to a solution of 6.2 g of the product of Step A in 70 ml of benzene and the mixture was refluxed for 90 minutes while removing the water of reaction by passing the condensed solvent through silica gel to obtain a solution of (1R,4R,5S) 4-[dihydro-2-oxo-3-(2H)-thienyl]-6,6-dimethyl-3-oxabicyclo-(3,1,0)-hexan-2-one which was used as is for the next step.

Workup

  1. temperaturethe mixture was refluxed for 90 minutes
  2. customwhile removing
  3. customthe water of reaction

Sources & evidence

ORD record
ord-18edd09d14fe41349a5002b082b1a115
Source dataset
uspto-grants-1983_10
Patent number
US04412069

Reaction notes

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