Trifluoroacetic acid → HCID 11826692, compound
Reaction equation
[C:1]([O:7][CH2:8][C@H:9]([CH3:38])[CH2:10][C@H:11]([O:36][CH3:37])[C@@H:12]([O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])[C@@H:13]([O:26][CH3:27])[CH2:14][C@@H:15]([CH3:25])[CH2:16][O:17][Si](C(C)(C)C)(C)C)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].O1CCCC1.FC(F)(F)C(O)=O>O>[CH3:25][C@H:15]([CH2:14][C@H:13]([O:26][CH3:27])[C@H:12]([O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:30])[CH3:31])[C@@H:11]([O:36][CH3:37])[CH2:10][C@@H:9]([CH3:38])[CH2:8][O:7][C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3])[CH2:16][OH:17]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
Bis-t-butyldimethylsilyloxy ether 25 (3.67 g, 6.36 mmol) was dissolved in asolution composed of 54 ml of tetrahydrofuran, 18 ml of water, and 0.9 ml of trifluoroacetic acid. The mixture was stirred at 25° C. for 5 hr. The mixture was partitioned between 200 ml of methylene chloride and 100 ml of saturated sodium bicarbonate solution. The aqueous phase was extracted with 2×200 ml of methylene chloride. The organic layers were combined, dried over magnesium sulfate, and concentrated in vacuo to yield 3.75 g of an oil. The oil was purified by chromatography on 190 g ofsilica gel eluting with hexanes:ethyl acetate (4:1) to give 2.675 g of primary alcohol 26. This material was homogeneous by both 1H and 13C NMR.
Workup
- customThe mixture was partitioned between 200 ml of methylene chloride and 100 ml of saturated sodium bicarbonate solution
- extractionThe aqueous phase was extracted with 2×200 ml of methylene chloride
- dry with materialdried over magnesium sulfate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-b477564b1fe94698a9f4e37fa8a8afb0
- Source dataset
- uspto-grants-1995_08
- Patent number
- US05446158
Reaction notes
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