Tetrabutylammonium Fluoride → 14-(5-Methoxy-1H-indol-2-YL)tetradecan-1-OL
Reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[O:19]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][C:41]#[C:42][C:43]1[CH:48]=[C:47]([O:49][CH3:50])[CH:46]=[CH:45][C:44]=1[NH:51]C(=O)OC(C)(C)C)[Si](C(C)(C)C)(C)C>C1COCC1>[CH3:50][O:49][C:47]1[CH:48]=[C:43]2[C:44](=[CH:45][CH:46]=1)[NH:51][C:41]([CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][OH:19])=[CH:42]2Participants
4
Procedure
A mixture of 1M THF solution of TBAF (5.1 mL, 5.11 mmol, 15 eq) and tert-butyl {2-[16-(tert-butyl-dimethylsilanoxy)-hexadecynyl]-4-methoxyp henyl}-carbamate (195 mg, 0.34 mmol, 1 eq) was refluxed for 24 hours. After removing THF, the residue was diluted with 50 mL of water, and extracted three times with AcOEt (50 mL). The extract was washed with aqueous solution of sodium chloride, dried over magnesium sulfate, and concentrated. The resulting concentrate was subjected to silica gel flush chromatography (eluate: hexane-AcOEt=70-30) to give white solid of the title compound (79.1 mg, yield 81%).
Workup
- temperaturewas refluxed for 24 hours
- customAfter removing THF
- additionthe residue was diluted with 50 mL of water
- extractionextracted three times with AcOEt (50 mL)
- washThe extract was washed with aqueous solution of sodium chloride
- dry with materialdried over magnesium sulfate
- concentrationconcentrated
- concentrationThe resulting concentrate
- customflush chromatography (eluate: hexane-AcOEt=70-30)
Sources & evidence
- ORD record
- ord-076f456dd3724f8ca02a04fdd90ce9f4
- Source dataset
- uspto-grants-2007_12
- Patent number
- US07307098B2
Reaction notes
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