Tetrabutylammonium Fluoride → [3,5-Bis-methoxymethoxy-4-((E)-3-phenyl-allyl)-phenyl]-methanol
Reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:17]=[C:18]([O:29][CH2:30][O:31][CH3:32])[C:19]=1[CH2:20]/[CH:21]=[CH:22]/[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:8][O:9][Si](C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH3:32][O:31][CH2:30][O:29][C:18]1[CH:17]=[C:7]([CH2:8][OH:9])[CH:6]=[C:5]([O:4][CH2:3][O:2][CH3:1])[C:19]=1[CH2:20]/[CH:21]=[CH:22]/[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of [3,5-bis-methoxymethoxy-4-((E)-3-phenyl-allyl)-benzyloxy]-tert-butyl-dimethyl-silane (220d) (55 g, 0.12 mol) in THF (250 mL) was added TBAF (47.2 g, 0.18 mol) in one portion. The mixture was stirred at room temperature for 0.5 hr. TLC (EtOAc/petroleum ether=1/10) showed that the reaction was complete. The reaction mixture was washed with brine (50 mL) and the aqueous layer was extracted with EtOAc (2×100 mL). The combined organic layers were dried over Na2SO4 and concentrated in high vacuum to give the title compound (45 g, 92% yield) as a yellow oil. 1H NMR (400 MHz, CDCl3): δ 7.16˜7.41 (m, 5H), 6.82 (s, 2H), 6.47 (m, 2H), 5.22 (s, 4H), 4.71 (s, 2H), 3.62 (d, 2H), 3.45 (s, 6H).
Workup
- washThe reaction mixture was washed with brine (50 mL)
- extractionthe aqueous layer was extracted with EtOAc (2×100 mL)
- dry with materialThe combined organic layers were dried over Na2SO4
- concentrationconcentrated in high vacuum
Sources & evidence
- ORD record
- ord-d4ad71569fc6493ba95f270ca34c9806
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07842713B2
Reaction notes
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