Diethyl Ether → 1,1,1,3,3,3-hexafluoro-2-[1-(2-hydroxy-1-phenyl-ethyl)-2-methyl-2,3-dihydro-1H-indol-5-yl]-propan-2-ol

HRID 1724036Notes

Reaction equation

HRID 1724036 reaction equation
[CH3:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:11]([O:20][Si](CC)(CC)CC)([C:16]([F:19])([F:18])[F:17])[C:12]([F:15])([F:14])[F:13])[CH:8]=2)[N:3]1[CH:28]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:29][OH:30].CCCC[N+](CCCC)(CCCC)CCCC.[F-].CCOCC.[NH4+].[Cl-]>C1COCC1>[F:15][C:12]([F:13])([F:14])[C:11]([C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]([CH:28]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:29][OH:30])[CH:2]([CH3:1])[CH2:10]2)([OH:20])[C:16]([F:19])([F:18])[F:17]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 210822072-[2-Methyl-5-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-2,3-dihydro-indol-1-yl]-2-phenyl-ethanol

Product 1

HCID 115099761,1,1,3,3,3-hexafluoro-2-[1-(2-hydroxy-1-phenyl-ethyl)-2-methyl-2,3-dihydro-1H-indol-5-yl]-propan-2-olYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 19 mg (0.036 mmol) of 2-[2-methyl-5-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-2,3-dihydro-indol-1-yl]-2-phenyl-ethanol in 0.5 mL THF were added 0.043 mL (0.043 mmol) of a 1M TBAF solution in THF. After stirring at RT for 24 hrs the mixture was distributed between Et2O and a saturated aqueous solution of NH4Cl. The combined organic phases were dried over Na2SO4 and evaporated. Column chromatography on silica gel with n-heptane/EtOAc 2:1 yielded 9.3 mg (62%) of 1,1,1,3,3,3-hexafluoro-2-[1-(2-hydroxy-1-phenyl-ethyl)-2-methyl-2,3-dihydro-1H-indol-5-yl]-propan-2-ol, yellow viscous oil, MS: 420 (MH+).

Workup

  1. dry with materialThe combined organic phases were dried over Na2SO4
  2. customevaporated

Sources & evidence

ORD record
ord-82dc2a635c2440b8964cd25498e93317
Source dataset
uspto-grants-2009_02
Patent number
US07485652B2

Reaction notes

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