Dimethyl Sulfoxide → HCID 19073214, compound

HRID 1051319Notes

Reaction equation

HRID 1051319 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:18])[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=1.CS(C)=O.C(N(CC)CC)C.N1C=CC=CC=1.S(=O)(=O)=O>ClCCl.C(OCC)(=O)C.O>[C:12]1([CH2:11][C:10]([C:7]2[CH:6]=[CH:5][C:4]([C:3]([O:2][CH3:1])=[O:19])=[CH:9][CH:8]=2)=[O:18])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

8

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 168533Sulfur trioxide-pyridineHCID 15638768HCID 15638768, compound

Product 1

HCID 19073214HCID 19073214, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

33 g methyl-4-(1-hydroxy-2-phenylethyl)benzoate (prepared as described by Berk et al.; J. Org. Chem. 1988, 53, 5791) is dissolved in 200 mL of dichloromethane. The solution is cooled to 0-10° C. To this is added DMSO (10 eq) and triethylamine (1.5 eq) followed by addition of 1.5 eq of pyridine-sulphur trioxide-complex. The reaction is stirred overnight at RT 200 ml of water is added. Then ethyl acetate is added and the organic layer is separated, dried, and concentrated to obtain the crude compound. It is purified by column chromatography to obtain the desired compound.

Workup

  1. additionis added
  2. customthe organic layer is separated
  3. customdried
  4. concentrationconcentrated
  5. customto obtain the crude compound
  6. customIt is purified by column chromatography

Sources & evidence

ORD record
ord-15af648c310841f88625d4ef09750e9a
Source dataset
uspto-grants-2016_07
Patent number
US09387204B2

Reaction notes

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