2-(1-benzyl-2-hydroxymethyl-1H-indol-5-yl)-1,1,1,3,3,3-hexafluoro-propan-2-ol → 1-benzyl-5-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-1H-indole-2-carbaldehyde

HRID 346832Notes

Reaction equation

[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([OH:26])([C:22]([F:25])([F:24])[F:23])[C:18]([F:21])([F:20])[F:19])=[CH:14][CH:15]=2)[CH:10]=[C:9]1[CH2:27][OH:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1(C)C=CC=CC=1.O=[Mn]=O>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([OH:26])([C:22]([F:25])([F:23])[F:24])[C:18]([F:19])([F:20])[F:21])=[CH:14][CH:15]=2)[CH:10]=[C:9]1[CH:27]=[O:28])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 1.03 g (2.56 mmol) of 2-(1-benzyl-2-hydroxymethyl-1H-indol-5-yl)-1,1,1,3,3,3-hexafluoro-propan-2-ol (example 41) in 10 mL toluene were added 2.22 g (25.6 mmol) of MnO2 powder. The mixture was stirred at 80° C. overnight. Filtration through decalite, evaporation of the solvent and column chromatography on silica gel with n-heptane/EtOAc 3:1 yielded 0.342 g (33%) of 1-benzyl-5-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-1H-indole-2-carbaldehyde, MS: 400 (M−H)−.

Workup

filtrationFiltration
customthrough decalite, evaporation of the solvent and column chromatography on silica gel with n-heptane/EtOAc 3:1

Sources & evidence

ORD record: ord-d918723f005e47ad9c03be8345d3dc3a
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07173048B2

Reaction notes

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