7-(Hydroxymethyl)-4-(2-methyl-1,3-thiazol-4-yl)-2H-chromen-2-one → 4-(2-Methyl-1,3-thiazol-4-yl)-2-oxo-2H-chromene-7-carbaldehyde

HRID 1988217Notes

Reaction equation

HRID 1988217 reaction equation
[OH:1][CH2:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([C:14]3[N:15]=[C:16]([CH3:19])[S:17][CH:18]=3)=[CH:8][C:9](=[O:13])[O:10]2)=[CH:5][CH:4]=1>C(Cl)Cl.O=[Mn]=O>[CH3:19][C:16]1[S:17][CH:18]=[C:14]([C:7]2[C:6]3[C:11](=[CH:12][C:3]([CH:2]=[O:1])=[CH:4][CH:5]=3)[O:10][C:9](=[O:13])[CH:8]=2)[N:15]=1

Participants

4

Reactant 1

HCID 577292517-(Hydroxymethyl)-4-(2-methyl-1,3-thiazol-4-yl)-2H-chromen-2-one

Product 1

HCID 577292574-(2-Methyl-1,3-thiazol-4-yl)-2-oxo-2H-chromene-7-carbaldehyde

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-(hydroxymethyl)-4-(2-methyl-1,3-thiazol-4-yl)-2H-chromen-2-one (0.387 g, 1.42 mmol) in CH2Cl2 (7 ml) was added MnO2 (1.85 g, 21.2 mmol) and stirred at rt for 4 h. A second portion of MnO2 (1.85 g, 21.2 mmol) was added and 3 h later the reaction mixture was filtered on celite, evaporated to dryness and purified by trituration in CH2Cl2-MeOH (9:1) to give the title compound. 1H NMR (400 MHz, acetone-d6): δ 10.12 (s, 1H), 8.45 (m, 1H), 8.31 (s, 1H), 7.95 (s, 1H), 7.85 (m, 1H), 6.9 (s, 1H), 2.80 (s, 3H).

Workup

  1. filtrationwas filtered on celite
  2. customevaporated to dryness
  3. custompurified by trituration in CH2Cl2-MeOH (9:1)

Sources & evidence

ORD record
ord-d16784566d9b42ecbd58f50305375a07
Source dataset
uspto-grants-2009_06
Patent number
US07553973B2

Reaction notes

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