Tetrabutylammonium Fluoride → [3,5-Bis-methoxymethoxy-4-((E)-3-phenyl-allyl)-phenyl]-methanol

HRID 1643694Notes

Reaction equation

HRID 1643694 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]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66755605[3,5-Bis-methoxymethoxy-4-((E)-3-phenyl-allyl)-benzyloxy]-tert-butyl-dimethyl-silane

Product 1

HCID 66755849[3,5-Bis-methoxymethoxy-4-((E)-3-phenyl-allyl)-phenyl]-methanolYield 108.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. washThe reaction mixture was washed with brine (50 mL)
  2. extractionthe aqueous layer was extracted with EtOAc (2×100 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated in high vacuum

Sources & evidence

ORD record
ord-73ad8d9671cd4f14a59fd90a5ef1288c
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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