Dimethyl Sulfoxide → HCID 22117848, compound

HRID 1799221Notes

Reaction equation

HRID 1799221 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][C:3]=1[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C.N1C=CC=CC=1.S(=O)(=O)=O.CS(C)=O>CCOCC.ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][C:3]=1[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 168533Sulfur trioxide-pyridineHCID 66724752HCID 66724752, compound

Product 1

HCID 22117848HCID 22117848, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

4-Chloro-3-(phenylmethoxy)phenyl methan-1-ol (82c) (2.74 g, 11.06 mmol) was dissolved in 25 mL ether. Triethylamine (TEA) (7.74 mL, 55.3 mmol) was added and the mixture was cooled to 0° C. A suspension of sulfur trioxide-pyridine (5.27 g, 22.18 mmol) and dimethylsulfoxide (6.3 mL, 88.48 mmol) was added dropwise. The reaction mixture was warmed to room temperature and stirred for 1 hour. The reaction mixture was then diluted with dichloromethane, washed with 1N hydrochloric acid, sodium bicarbonate and brine and concentrated to dryness. The crude product was purified by preparative HPLC using hexane/ethyl acetate to give the 1.9 g (71% yield) of the title compound (82d).

Workup

  1. additionwas added dropwise
  2. temperatureThe reaction mixture was warmed to room temperature
  3. washwashed with 1N hydrochloric acid, sodium bicarbonate and brine
  4. concentrationconcentrated to dryness
  5. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-9520ec460aeb4aeb86dc80bfa027d649
Source dataset
uspto-grants-2013_01
Patent number
US08344028B2

Reaction notes

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