Dimethyl Sulfide → Methyl 2-{[2-(4-hydroxyphenyl)ethyl]thio}-3-[4-(2-{4-[(methylsulfonyl)oxy]phenoxy}ethyl)phenyl]propanoate

HRID 1178567Notes

Reaction equation

HRID 1178567 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][S:17][CH:18]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][O:32][C:33]3[CH:38]=[CH:37][C:36]([O:39][S:40]([CH3:43])(=[O:42])=[O:41])=[CH:35][CH:34]=3)=[CH:26][CH:25]=2)[C:19]([O:21][CH3:22])=[O:20])=[CH:11][CH:10]=1)C1C=CC=CC=1.ClCCl.CSC.B(F)(F)F.CCOCC>O>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][S:17][CH:18]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][O:32][C:33]3[CH:34]=[CH:35][C:36]([O:39][S:40]([CH3:43])(=[O:42])=[O:41])=[CH:37][CH:38]=3)=[CH:26][CH:25]=2)[C:19]([O:21][CH3:22])=[O:20])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 1068Dimethyl SulfideHCID 6344DichloromethaneHCID 8000Boron trifluoride etherateHCID 86600805HCID 86600805, compound

Product 1

HCID 73017203Methyl 2-{[2-(4-hydroxyphenyl)ethyl]thio}-3-[4-(2-{4-[(methylsulfonyl)oxy]phenoxy}ethyl)phenyl]propanoateYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of methyl 2-({2-[4-(benzyloxy)phenyl]ethyl}thio)-3-[4-(2-{4-[(methylsulfonyl)oxy]phenoxy}ethyl)phenyl]propanoate (477 mg, 0.8 mmol) and 15 ml dichlormethane, dimethyl sulfide (239 mg, 3.8 mol) and boron trifluoride etherate (545 mg, 3.8 mmol) were added. After 18 hours of stirring water was added to the reaction. The phases were separated and the aqueous phase was extracted twice with dichlormethane. The organic phases were pooled, dried (MgSO4) and evaporated under reduced pressure. 274 mg of the desired product (yield 67%) was obtained as an oil.

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted twice with dichlormethane
  3. dry with materialdried (MgSO4)
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-504a9bbb02184dd7af6c7afcce10b1d5
Source dataset
uspto-grants-2007_10
Patent number
US07276539B2

Reaction notes

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