Water → HCID 57436873, compound

HRID 1724004Notes

Reaction equation

HRID 1724004 reaction equation
[CH3:1][C:2]1([CH3:27])[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12](=[O:26])[CH2:13][C:14]3[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=3)[CH:8]=2)[O:3]1.[S:28](Cl)([C:31]1[CH:37]=[CH:36][C:34]([CH3:35])=[CH:33][CH:32]=1)(=[O:30])=[O:29].[OH2:39]>ClCCl.CN(C1C=CN=CC=1)C>[CH3:1][C:2]1([CH3:27])[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12](=[O:26])[CH:13]([O:29][S:28]([C:31]3[CH:37]=[CH:36][C:34]([CH3:35])=[CH:33][CH:32]=3)(=[O:39])=[O:30])[C:14]3[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=3)[CH:8]=2)[O:3]1

Participants

6

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 9799516HCID 9799516, compound

Product 1

HCID 57436873HCID 57436873, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution [1-(2,2-dimethyl-chroman-6-yl)-2-(3,4,5-trimethoxy-phenyl)-ethanone (3.4 mg, 0.009 mmol) dissolved in anhydrous dichloromethane (1.0 mL) is added TsCl (1.94 mg, 0.011 mmol), DMAP (1.24 mg, 0.011 mmol) and TEA (21.3 μL, 0.015 mmol). The reaction mixture continues stirring at room temperature overnight. The next day, the reaction mixture is diluted with water. The aqueous layer is separated and extracted with ethyl acetate (3×). All combined organic layers are dried over Na2SO4, filtered, and concentrated to yield an oil. The crude material is purified using silica gel chromatography to yield the desired product.

Workup

  1. customThe aqueous layer is separated
  2. extractionextracted with ethyl acetate (3×)
  3. dry with materialAll combined organic layers are dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto yield an oil
  7. customThe crude material is purified

Sources & evidence

ORD record
ord-324137cf87a546e692aa5efd4c882b7e
Source dataset
uspto-grants-2009_02
Patent number
US07485283B2

Reaction notes

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