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

HRID 1362410Notes

Reaction equation

HRID 1362410 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-5b7147c31cb34f39bdea4c75b5a1f8b8
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

Loading…