[1-(2-Trimethylsilanyl-ethanesulfonyl)-1H-indol-5-yl]-methanol → 1-(2-Trimethylsilanyl-ethanesulfonyl)-1H-indole-5-carbaldehyde

HRID 2355847Notes

Reaction equation

[CH3:1][Si:2]([CH3:20])([CH3:19])[CH2:3][CH2:4][S:5]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:17][OH:18])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)(=[O:7])=[O:6]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:1][Si:2]([CH3:20])([CH3:19])[CH2:3][CH2:4][S:5]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH:17]=[O:18])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)(=[O:7])=[O:6]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of [1-(2-trimethylsilanyl-ethanesulfonyl)-1H-indol-5-yl]-methanol (2.1 g, 6.74 mmol) in methylene chloride (30 mL) was added at 0° C. to a mixture of activated manganese dioxide (22 g, azeotropically dried with toluene (2×)) and methylene chloride (70 mL) in a 500 mL round bottom flask. The reaction mixture was stirred at 0° C. for 30 min and filtered through a pad of celite. Solvents were removed in vacuo to afford the title compound as a white solid (1.8 g, 80%). 1H-NMR (CDCl3, 500 MHz) δ 10.06 (s, 1H), 8.15 (s, 1H), 8.01 (d, J=8.6 Hz, 1H), 7.87 (dd, J=8.6, 1.5 Hz, 1H), 7.54 (d, J=3.4 Hz, 1H), 6.80 (d, J=3.6 Hz, 1H), 3.24-3.20 (m, 2H), 0.86-0.82 (m, 2H), −0.06 (s, 9H). 13C-NMR (CDCl3, 125 MHz) δ 191.9, 138.5, 132.3, 130.7, 128.8, 125.3, 125.1, 1134.6, 108.4, 51.4, 10.2, −2.1. Mass spec. 310.12 (MH)+.

Workup

dry with materialazeotropically dried with toluene (2×)) and methylene chloride (70 mL) in a 500 mL round bottom flask
filtrationfiltered through a pad of celite
customSolvents were removed in vacuo

Sources & evidence

ORD record: ord-c7b7184d47094608aaa2c7e9515d2d10
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07754732B2

Reaction notes

Loading…