(4-{[(2-Phenylethyl)(4-phenyl-1,3-thiazol-2-yl)amino]methyl}phenyl)methanol → 4-{[(2-Phenylethyl)(4-phenyl-1,3-thiazol-2-yl)amino]methyl}benzaldehyde

HRID 507931Notes

Reaction equation

HRID 507931 reaction equation
[C:1]1([CH2:7][CH2:8][N:9]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([CH2:28][OH:29])=[CH:24][CH:23]=2)[C:10]2[S:11][CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>O1CCCC1.[O-2].[O-2].[Mn+4]>[C:1]1([CH2:7][CH2:8][N:9]([CH2:21][C:22]2[CH:23]=[CH:24][C:25]([CH:28]=[O:29])=[CH:26][CH:27]=2)[C:10]2[S:11][CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:14]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 23111783(4-{[(2-Phenylethyl)(4-phenyl-1,3-thiazol-2-yl)amino]methyl}phenyl)methanol

Product 1

HCID 231573484-{[(2-Phenylethyl)(4-phenyl-1,3-thiazol-2-yl)amino]methyl}benzaldehydeYield 68%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4-{[(2-phenylethyl)(4-phenyl-1,3-thiazol-2-yl)amino]methyl}phenyl)methanol (3.0 g, 7.49 mmol) in tetrahydrofuran (50 mL) was added manganese dioxide (1.95 g, 22.5 mmol), and the mixture was stirred at room temperature for 3 hr. The insoluble material was filtered off and the filtrate was concentrated. The residue was purified by silica gel column chromatography (5%-50% ethyl acetate/hexane) to give the title compound (2.02 g, yield 68%) as a colorless oil.

Workup

  1. filtrationThe insoluble material was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by silica gel column chromatography (5%-50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-9420b480468d4b9caf4dac459ecbeef8
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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