p-Toluenesulfonic acid → HCID 57009145, compound

HRID 2210648Notes

Reaction equation

HRID 2210648 reaction equation
[OH:1][CH2:2][C@@H:3]1[C@@H:7]([CH3:8])[CH2:6][CH2:5][C@@H:4]1[C@@H:9]([CH3:12])[CH2:10][OH:11].[C:13]1(C)[CH:18]=CC(S(O)(=O)=O)=C[CH:14]=1.C(OCC)(=O)C>ClCCl.COC(OC)(C)C>[CH3:14][C:13]1([CH3:18])[O:11][CH2:10][C@H:9]([CH3:12])[C@H:4]2[C@@H:3]([C@@H:7]([CH3:8])[CH2:6][CH2:5]2)[CH2:2][O:1]1

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 57023068HCID 57023068, compound

Product 1

HCID 57009145HCID 57009145, compoundYield 162.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 64952,2-DimethoxypropaneSolvent

Procedure

(2R)-2-[(1R, 2R, 3S)-2-(hydroxymethyl)-3-methylcyclopent-1-yl]propan-1-ol (100 mg, 0.00058 mol) (obtained in Definite Example 45) was dissolved in 5 mι of dichloromethane, and 2 mι of 2, 2-dimethoxypropan and 5 mg of p-toluenesulfonic acid were added. After being stirred at room temperature for 12 hours, the reaction mixture was poured into 50 mι of ethyl acetate. After the organic layer was washed with an aqueous mixed solution of aqueous sodium bicarbonate (10 mι) and saturated sodium chloride solution (20 mι), it was dried by magnesium sulfate, filtered, and then concentrated under a reduced pressure. The residual substance was purified by a chromatography using silica gel. When the solvent of the fraction obtained from hexane:ether=8:2 eluent was distilled off, a colorless oily substance, i.e., (1R, 7R, 8S, 11S)-4, 4, 7, 11-tetramethyl-3, 5-dioxabicyclo[6. 3. 0]undecane (10 mg, yield=7.9%). This (1R, 7R, 8S, 11S)-4, 4, 7, 11-tetramethyl-3, 5-dioxabicyclo[6.3.0]undecane had the following physicochemical properties:

Workup

  1. additionwere added
  2. washAfter the organic layer was washed with an aqueous mixed solution of aqueous sodium bicarbonate (10 mι) and saturated sodium chloride solution (20 mι), it
  3. dry with materialwas dried by magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under a reduced pressure
  6. customThe residual substance was purified by a chromatography
  7. customWhen the solvent of the fraction obtained from hexane
  8. distillationether=8:2 eluent was distilled off

Sources & evidence

ORD record
ord-b1a484d5264b42e0ab9750a98f9ea693
Source dataset
uspto-grants-1995_10
Patent number
US05459160

Reaction notes

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