Ethanethiol → 7-Hydroxy-4-methyl-3-pyridin-4-yl-chromen-2-one

HRID 747866

Reaction equation

HRID 747866 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([CH3:20])=[C:8]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)[C:9](=[O:13])[O:10]2)=[CH:5][CH:4]=1.CCS.[Al](Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([CH3:20])=[C:8]([C:14]3[CH:15]=[CH:16][N:17]=[CH:18][CH:19]=3)[C:9](=[O:13])[O:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 24409Aluminum bromideHCID 116590187-Methoxy-4-methyl-3-pyridin-4-yl-chromen-2-one

Product 1

HCID 1355029137-Hydroxy-4-methyl-3-pyridin-4-yl-chromen-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-methoxy-4-methyl-3-pyridin-4-yl-chromen-2-one (600 mg, 2.24 mmoL) in CH2Cl2 (10 mL) at 0° C. was added EtSH (˜1 mL) followed by AlBr3 (6.74 mmoL, 1.80 g). The mixture was slowly warm to room temperature and poured into ice sat. NaHCO3 solution. Extraction was conducted 3× with CH2Cl2. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to give the crude material, which was then purified by silica gel column chromatography using hexanes:ethyl acetate 1:1 as eluent to afford the title product as pale yellow solid.

Workup

  1. additionpoured into ice sat. NaHCO3 solution
  2. extractionExtraction
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the crude material, which
  8. customwas then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2f8b5397725240e8bf29bd29c8541eb3
Source dataset
uspto-grants-2008_07
Patent number
US07399767B2

Linked notes

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