Dichloromethane → HCID 86672565, compound

HRID 1918382Notes

Reaction equation

HRID 1918382 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.C(Cl)Cl.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>N1C=CC=CC=1>[O:1]1[CH2:4][CH:3]([C:5]2[CH:6]=[C:7]([CH2:11][CH2:12][O:13][S:23]([C:20]3[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=3)(=[O:25])=[O:24])[CH:8]=[CH:9][CH:10]=2)[CH2:2]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 73974-Toluenesulfonyl chlorideHCID 671700292-(3-Oxetan-3-yl-phenyl)-ethanol

Product 1

HCID 86672565HCID 86672565, compoundYield 21.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4.9 g of 2-(3-Oxetan-3-yl-phenyl)-ethanol were dissolved using 30 ml of CH2Cl2 and 9.5 ml of pyridine added. Then, 6.3 g of p-toluenesulfonyl chloride was added at 0° C. and the reaction mixture stirred for 6 h at room temperature. The reaction mixture was then evaporated, re-dissolved using 100 ml of EA and washed using 100 ml of a saturated aqueous NaHCO3-solution. The aqueous layer was then extracted twice using 100 ml of EA each. The combined organic layer was then dried using MgSO4 and evaporated. Chromatography on silica gel using EA/HEP 1:1 yielded 2.0 g of the title compound, colorless oil.

Workup

  1. additionadded
  2. customThe reaction mixture was then evaporated
  3. dissolutionre-dissolved
  4. washwashed
  5. extractionThe aqueous layer was then extracted twice
  6. customThe combined organic layer was then dried
  7. customevaporated

Sources & evidence

ORD record
ord-a64ee9dee45e46289fab33039097f047
Source dataset
uspto-grants-2013_12
Patent number
US08618304B2

Reaction notes

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