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

HRID 1749224Notes

Reaction equation

HRID 1749224 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 4 A 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-6d8994bea6a443a68083f258c301a568
Source dataset
uspto-grants-2015_10
Patent number
US09156810B2

Reaction notes

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