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

HRID 406795

Reaction equation

HRID 406795 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-1a7ba306a4944da791246b5d6332cddc
Source dataset
uspto-grants-2014_06
Patent number
US08754122B2

Linked notes

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