Tetrabutylammonium Fluoride → HCID 20253400, compound
Reaction equation
[O:1]([CH2:9][CH2:10][C:11]#[C:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH:19]([OH:21])[CH3:20])[Si](C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.O>[OH:1][CH2:9][CH2:10][C:11]#[C:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH:19]([OH:21])[CH3:20]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 23 °C
Procedure
To a solution of 19 (2.9 g, 9.4 mmol) in THF (15 mL) was added 19 mL of tetra-n-butylammonium fluoride (19 mmole, 1M solution in THF). The reaction was stirred for 1 hr at 23° C. then diluted with 75 mL of water. The aqueous mixture was extracted with ether (3×50 mL) and the ether extract washed with brine (2×50 mL). Product isolation yielded 1.86 g (100%) of the diol (20). No further purification was carried out on 20.
Workup
- extractionThe aqueous mixture was extracted with ether (3×50 mL)
- extractionthe ether extract
- washwashed with brine (2×50 mL)
Sources & evidence
- ORD record
- ord-ed5b50673ac347c68094961d662cc76f
- Source dataset
- uspto-grants-1985_12
- Patent number
- US04560551
Reaction notes
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