Methyl morpholine oxide → 3-Chloro-1-benzothiophene-2-carbaldehyde

HRID 2264634Notes

Reaction equation

HRID 2264634 reaction equation
[Cl:1][C:2]1[C:3]2[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=2[S:5][C:6]=1[CH2:7][OH:8].C[N+]1([O-])CCOCC1>C(Cl)Cl.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[Cl:1][C:2]1[C:3]2[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=2[S:5][C:6]=1[CH:7]=[O:8]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 821965(3-Chloro-1-benzothien-2-yl)methanol

Product 1

HCID 8181213-Chloro-1-benzothiophene-2-carbaldehydeYield 84.7%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of alcohol 12 (4.32 g, 21.6 mmol) in 40 mL of CH2Cl2 was treated with 4A molecular sieves, NMO (3.81 g, 32.5 mmol), and TPAP (381 mg, 1.08 mmol). The reaction was stirred for 10 min. and then was evaporated to dryness. Purification by flash chromatography on silica gel (2% ethyl acetate/hexane) gave 3.52 g (18.3 mmol, 84%) of the aldehyde (13).

Workup

  1. customwas evaporated to dryness
  2. customPurification by flash chromatography on silica gel (2% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-5f39539d3b4e44878140a47d519bbad7
Source dataset
uspto-grants-2010_12
Patent number
US07855226B2

Reaction notes

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