[4-Chloro-3-(1,1-dioxo-1lambda6-thiomorpholin-4-yl)-5-ethoxy-phenyl]-methanol → 4-Chloro-3-(1,1-dioxo-1lambda6-thiomorpholin-4-yl)-5-ethoxy-benzaldehyde

HRID 1990866Notes

Reaction equation

HRID 1990866 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH2:9][CH3:10])=[CH:6][C:5]([CH2:11][OH:12])=[CH:4][C:3]=1[N:13]1[CH2:18][CH2:17][S:16](=[O:20])(=[O:19])[CH2:15][CH2:14]1>C1COCC1.O=[Mn]=O>[Cl:1][C:2]1[C:7]([O:8][CH2:9][CH3:10])=[CH:6][C:5]([CH:11]=[O:12])=[CH:4][C:3]=1[N:13]1[CH2:14][CH2:15][S:16](=[O:20])(=[O:19])[CH2:17][CH2:18]1

Participants

4

Reactant 1

HCID 68694740[4-Chloro-3-(1,1-dioxo-1lambda6-thiomorpholin-4-yl)-5-ethoxy-phenyl]-methanol

Product 1

HCID 587063474-Chloro-3-(1,1-dioxo-1lambda6-thiomorpholin-4-yl)-5-ethoxy-benzaldehydeYield 95%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [4-chloro-3-(1,1-dioxo-1λ6-thiomorpholin-4-yl)-5-ethoxy-phenyl]-methanol (0.089 g, 0.28 mmol, 1.0 equiv) in THF (20 mL) was added activated MnO2 (0.242 g, 2.78 mmol, 10.0 equiv). After stirring at rt for 4 h, the reaction mixture was filtered and the solvent removed by evaporation under reduced pressure providing 0.084 g (95%) of the title compound in sufficient quality for the reductive alkylation step. MS (ISP): 318.0 [M+H]+.

Workup

  1. filtrationthe reaction mixture was filtered
  2. customthe solvent removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-f51715c05c384ac4a6028506aa2adeeb
Source dataset
uspto-grants-2010_01
Patent number
US07645753B2

Reaction notes

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