p-Toluenesulfonic acid monohydrate → HCID 57989274, compound

HRID 1689554Notes

Reaction equation

HRID 1689554 reaction equation
[CH3:1][C:2]([CH3:22])([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15]C1CCCCO1)[CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.C(OCC)(=O)C.O>[OH:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:2]([CH3:1])([CH3:22])[CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

6

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 57989384HCID 57989384, compound

Product 1

HCID 57989274HCID 57989274, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 4,4-dimethyl-9-(tetrahydro-2H-pyran-2-yloxy)nonanoate (example 285, step e) (0.86 g) in methanol (10 mL) was added p-toluenesulfonic acid monohydrate (52 mg) and the reaction mixture was stirred at room temperature for 2 hours. The mixture was diluted with ethyl acetate and water and the phases separated. The aqueous layer was extracted with ethyl acetate (×2) and the combined organic phase was washed with 10% citric acid, saturated aqueous sodium bicarbonate solution and brine then dried over magnesium sulfate, filtered and evaporated. Purification was by silica gel chromatography eluting with 0-50% ethyl acetate in cyclohexane to afford the subtitled compound as colourless oil. Yield 0.44 g.

Workup

  1. customthe phases separated
  2. extractionThe aqueous layer was extracted with ethyl acetate (×2)
  3. washthe combined organic phase was washed with 10% citric acid, saturated aqueous sodium bicarbonate solution and brine
  4. dry with materialthen dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customPurification
  8. washeluting with 0-50% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-b2cbe68c627d4bd0b168eccb12e6f12b
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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