p-Toluenesulfonic acid → HCID 57264927, compound

HRID 2210660Notes

Reaction equation

HRID 2210660 reaction equation
[CH3:1][O:2][C:3]([O:6][CH3:7])([CH3:5])[CH3:4].[C:8]1([CH3:18])[CH:13]=[CH:12][C:11](S(O)(=O)=O)=[CH:10][CH:9]=1.[C:19](OCC)(=O)C>ClCCl>[CH3:4][C:3]1([CH3:5])[O:6][CH2:7][C:10](=[CH2:9])[C@@H:11]2[C@@H:19]([C@H:8]([CH3:18])[CH2:13][CH2:12]2)[CH2:1][O:2]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 8857Ethyl Acetate

Product 1

HCID 57264927HCID 57264927, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-[(1S, 2R, 3R)-2-(hydroxymethyl)-3-methylcyclopent-1-yl]-2-propen-1-ol (100 mg, 0.00059 mol) obtained in Definite Example 47 was dissolved in 3 mι of dichloromethane, and after 2 mι of 2,2-dimethoxypropane was added, 5 mg of p-toluenesulfonic acid wad added. The reaction mixture was stirred at room temperature for 12 hours. The reaction mixture was poured into 50 mι of ethyl acetate, and organic layer was washed with a mixed aqueous solution of saturated sodium bicarbonate solution (10 mι) and saturated sodium chloride solution (20 mι), was dried by adding magnesium sulfate, was filtered and was thereafter concentrated under a reduced pressure. The residual matter was purified by chromatography using silica gel, and the solvent of the fraction obtained from hexane:ether=9:1 eluent was distilled off. A colorless oily substance was thus obtained, i.e., (1R, 8S, 11R)-4, 4, 11-trimethyl-7-methylene-3, 5-dioxabicyclo[6.3.0]undecane (108 mg, yield=87.4%). This (1R, 8S, 11R)-4,4, 11-trimethyl-7-methylene-3, 5-dioxabicyclo[6, 3, 0]undecane had the following physicochemical properties:

Workup

  1. washwas washed with a mixed aqueous solution of saturated sodium bicarbonate solution (10 mι) and saturated sodium chloride solution (20 mι)
  2. customwas dried
  3. additionby adding magnesium sulfate
  4. filtrationwas filtered
  5. concentrationwas thereafter concentrated under a reduced pressure
  6. customThe residual matter was purified by chromatography
  7. customthe solvent of the fraction obtained from hexane
  8. distillationether=9:1 eluent was distilled off
  9. customA colorless oily substance was thus obtained

Sources & evidence

ORD record
ord-f00d9343a3d645d5b04af86c3a644f2d
Source dataset
uspto-grants-1995_10
Patent number
US05459160

Reaction notes

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