Pyridine → HCID 86672565, compound

HRID 1918327Notes

Reaction equation

HRID 1918327 reaction equation
[O:1]1[CH2:4][CH:3]([C:5]2[CH:6]=[C:7]([CH2:11][CH2:12][OH:13])[CH:8]=[CH:9][CH:10]=2)[CH2:2]1.N1C=CC=CC=1.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>C(Cl)Cl>[O:1]1[CH2:4][CH:3]([C:5]2[CH:6]=[C:7]([CH2:11][CH2:12][O:13][S:26]([C:23]3[CH:24]=[CH:25][C:20]([CH3:30])=[CH:21][CH:22]=3)(=[O:28])=[O:27])[CH:8]=[CH:9][CH:10]=2)[CH2:2]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 671700292-(3-Oxetan-3-yl-phenyl)-ethanol

Product 1

HCID 86672565HCID 86672565, compoundYield 21.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

4.9 g of 2-(3-oxetan-3-yl-phenyl)-ethanol were dissolved in 30 ml of DCM and 9.5 ml of pyridine were added at room temperature. The mixture was cooled to 0° C. and 6.3 g of p-toluenesulfonyl chloride were added at 0° C. Stirring was continued for 6 h at room temperature. Then the volatiles were evaporated, the residue was dissolved in 100 ml of EA and washed with 100 ml of a saturated aqueous solution of sodium hydrogencarbonate. The aqueous layer was extracted two times with 100 ml each of EA. The combined organic layers were dried with magnesium sulfate and evaporated. Silica gel chromatography (EA/HEP 1:1) of the residue yielded 2.0 g of the title compound.

Workup

  1. customThen the volatiles were evaporated
  2. dissolutionthe residue was dissolved in 100 ml of EA
  3. washwashed with 100 ml of a saturated aqueous solution of sodium hydrogencarbonate
  4. extractionThe aqueous layer was extracted two times with 100 ml each of EA
  5. dry with materialThe combined organic layers were dried with magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-f7c511e0aee94c6ba72b2ebbc942f2e2
Source dataset
uspto-grants-2013_12
Patent number
US08618304B2

Reaction notes

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