1-Benzothiophen-5-ylmethanol → Benzo(b)thiophene-5-carboxaldehyde

HRID 2097158Notes

Reaction equation

HRID 2097158 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([CH2:10][OH:11])[CH:8]=[CH:9][C:2]1=2>C1C=CC=CC=1.O=[Mn]=O>[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([CH:10]=[O:11])[CH:8]=[CH:9][C:2]1=2

Participants

4

Reactant 1

HCID 27954461-Benzothiophen-5-ylmethanol

Product 1

HCID 139097Benzo(b)thiophene-5-carboxaldehydeYield 92.6%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 241BenzeneSolvent

Procedure

Benzo[b]thiophen-5-ylmethanol (311 mg, 1.89 mmol) was dissolved in anhydrous benzene (20 mL). MnO2 (1317 mg, 15.2 mmol) was added and the reaction was stirred for 12 h. The solution was filtered through celite and the filter cake was washed with ethyl acetate (50 mL). The filtrate was concentrated under vacuum to give the product (284 mg, 92%) as an off-white solid: 1H NMR (400 MHz, DMSO-d6) δ 10.09 (s, 1H), 8.46-8.45 (m, 1H), 8.21 (d, J=8.4 Hz, 1H), 7.94 (d, J=5.6 Hz, 1H), 7.81 (dd, J=8.4, 1.2 Hz, 1H), 7.66 (d, J=5.6 Hz, 1H).

Workup

  1. filtrationThe solution was filtered through celite
  2. washthe filter cake was washed with ethyl acetate (50 mL)
  3. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-5525e1371e8143b8a4987fd5db6a2e90
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

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