HCID 59774862, compound → HCID 59774864, compound

HRID 2422512Notes

Reaction equation

HRID 2422512 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:6]=1[CH:12]([C:14]1[S:15][CH:16]=[CH:17][N:18]=1)[OH:13]>ClCCl.O=[Mn]=O>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:6]=1[C:12]([C:14]1[S:15][CH:16]=[CH:17][N:18]=1)=[O:13]

Participants

4

Reactant 1

HCID 59774862HCID 59774862, compound

Product 1

HCID 59774864HCID 59774864, compound

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of [2-(methoxymethoxy)-4-methylphenyl](1,3-thiazol-2-yl)methanol from step 1 (3.6 g, 13.7 mmol) and MnO2 (8.28 g, 95.2 mmol) in dichloromethane was stirred at room temperature overnight, filtered, and the insoluble material washed well with boiling EtOAc. The filtrates were combined and concentrated in vacuo to afford the title compound. 1H NMR (400 MHz, acetone-d6): 8.07-8.03 (m, 2H), 7.50 (d, 1H), 7.10 (s, 1H), 6.95 (d, 1H), 5.11 (s, 2H), 3.34 (s, 3H), 2.41 (s, 3H).

Workup

  1. filtrationfiltered
  2. washthe insoluble material washed well with boiling EtOAc
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6fb9d749276242d4bdd1ca62b42ff833
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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