4-Toluenesulfonyl chloride → HCID 67003408, compound

HRID 2362631Notes

Reaction equation

HRID 2362631 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][O:8][C:9]([C:14]2[S:15][CH:16]=[CH:17][N:18]=2)([CH2:12][OH:13])[CH2:10]O)=[CH:5][CH:4]=1.C([Li])CCC.C1(C)C=CC(S(Cl)(=O)=O)=CC=1>O1CCCC1>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][O:8][C:9]2([C:14]3[S:15][CH:16]=[CH:17][N:18]=3)[CH2:12][O:13][CH2:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 67002700HCID 67002700, compoundHCID 178418339Butyllithium2×

Product 1

HCID 67003408HCID 67003408, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
65 °C

Procedure

To a cold (0° C.) solution of 2-(4-methoxybenzyloxy)-2-(thiazol-2-yl)propane-1,3-diol (Example 11C) (4.02 g, 13.61 mmol) in tetrahydrofuran (120 mL) was added n-butyllithium (5.4 mL, 13.6 mmol, 2.5 M solution in hexane) dropwise. After 0.5 hours, a solution of para-toluenesulfonyl chloride (2.59 g, 13.61 mmol) in tetrahydrofuran (16 mL) was added to the suspension. The reaction was stirred for an additional 0.5 hours. Thereafter, n-butyllithium (5.4 mL, 13.6 mmol, 2.5 M solution in hexane) was added to the reacton dropwise, and the reaction was heated to 65° C. for 1 hour. The reaction was cooled to room temperature and quenched by the addition of water and ethyl acetate. The layers were separated, and the aqueous layer was extracted with additional ethyl acetate (2×). The combined organics were dried with anhydrous sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography on silica gel, eluting with a gradient of 0 to 30% ethyl acetate in hexane, to give the title product. MS ESI(+) m/z 278.3 [M+H]+;

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customquenched by the addition of water and ethyl acetate
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with additional ethyl acetate (2×)
  5. dry with materialThe combined organics were dried with anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography on silica gel
  9. washeluting with a gradient of 0 to 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-5b1c2a6848de490d8b0a4f974c2e0891
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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