Water → 77927-91-4

HRID 1421075Notes

Reaction equation

HRID 1421075 reaction equation
O[C:2]([CH3:16])(C)[C:3]([C:5]1C=CC(S(C)(=O)=O)=CC=1)=[O:4].CC(C)[C:19]([C:21]1C=CC(SC)=CC=1)=[O:20].[OH2:30]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:5][CH:3]([O:4][CH2:21][C:19]([OH:30])=[O:20])[CH:2]=[CH2:16]

Participants

6

Reactant 3

HCID 962WaterHCID 8525392-Methyl-1-[4-(methylthio)phenyl]-1-propanoneHCID 154285142-Hydroxy-2-methyl-1-(4-(methylsulfonyl)phenyl)propan-1-one

Product 1

HCID 1264884277927-91-4

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of the alcohol of Step 3 (2.87 g, 11.8 mmol) and the acid from step 1 (2.0 g, 15.4 mmol) in CH2Cl2 (30 mL) was added CMC (7.5 g, 17.7 mmol), along with 50 mg of DMAP. After stirring overnight, H2O (20 mL) was ad ded and the product was extracted with CH2Cl2. The organic layer was dried (MgSO4), filtered and evaporated. Purification was effected by flash chromatography (1:5 EtOAc:hexane) to yield 2.97 g of an oil.

Workup

  1. extractionthe product was extracted with CH2Cl2
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customPurification

Sources & evidence

ORD record
ord-1f709676e2ee4e65a31ffe2bfc487f7a
Source dataset
uspto-grants-2000_06
Patent number
US06071954

Reaction notes

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