Water → 2-(4-(4-Tosyloxybutyl)phenyl methyl)thio 3-methyl chromen-4-one

HRID 1723965Notes

Reaction equation

HRID 1723965 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][S:13][C:14]2[O:15][C:16]3[C:21]([C:22](=[O:25])[C:23]=2[CH3:24])=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:8][CH:7]=1.N1C=CC=C[CH:27]=1.[C:32]1(C)[C:33]([S:38](Cl)(=[O:40])=[O:39])=[CH:34][CH:35]=[CH:36][CH:37]=1.O>C(OCC)(=O)C>[S:38]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][S:13][C:14]2[O:15][C:16]3[C:21]([C:22](=[O:25])[C:23]=2[CH3:24])=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:8][CH:7]=1)([C:33]1[CH:32]=[CH:37][C:36]([CH3:27])=[CH:35][CH:34]=1)(=[O:39])=[O:40]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 8623o-Toluenesulfonyl chlorideHCID 177558312-(4-(4-Hydroxybutyl)phenyl methyl)thio 3-methyl chromen-4-one

Product 1

HCID 177561742-(4-(4-Tosyloxybutyl)phenyl methyl)thio 3-methyl chromen-4-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A 50 mL round bottom flask is charged with 2-(4-(4-hydroxybutyl)phenyl methyl)thio 3-methyl chromen-4-one (6.0 g, 16.9 mmol) and pyridine (15 mL) is added to it. Toluenesulfonyl chloride (25.4 mmol) is then added in one lot and the mixture is stirred for 8 hours after which water and ethyl acetate are added to it. The contents are poured into a separatory funnel and the layers separated. The organic layer is washed with 5% CuSO4 (2×10 mL) and then with water and brine. It is then dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue obtained is purified by silica gel flash chromatography (ethyl acetate:hexanes) to afford the product.

Workup

  1. additionis added to it
  2. additionare added to it
  3. additionThe contents are poured into a separatory funnel
  4. customthe layers separated
  5. washThe organic layer is washed with 5% CuSO4 (2×10 mL)
  6. dry with materialIt is then dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue obtained
  10. customis purified by silica gel flash chromatography (ethyl acetate:hexanes)
  11. customto afford the product

Sources & evidence

ORD record
ord-6d99e3cd1b404afda9be9575b34c7bb4
Source dataset
uspto-grants-2009_02
Patent number
US07485283B2

Reaction notes

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