Tetrabutylammonium Fluoride → HCID 68816698, compound

HRID 733298Notes

Reaction equation

HRID 733298 reaction equation
[Si]([O:8][C:9]1[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17](=[O:27])[C:18]([CH3:26])([CH3:25])[C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:11][C:10]=1[O:28][CH3:29])(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:8][C:9]1[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17](=[O:27])[C:18]([CH3:26])([CH3:25])[C:19](=[O:24])[C:20]([CH3:23])([CH3:21])[CH3:22])=[CH:11][C:10]=1[O:28][CH3:29]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68817206HCID 68817206, compound

Product 1

HCID 68816698HCID 68816698, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(E)-1-(4-tert-butyldimethylsilyloxy-3-methoxyphenyl)-4,4,6,6-tetramethylhept-1-ene-3,5-dione (266 mg, 0.635 mmol) was dissolved in anhydrous THF (10 ml) and stirred at room temperature under a nitrogen atmosphere. TBAF (0.22 ml, 0.76 mmol) was added (yellow/green solution goes deep red colour) and the mixture was stirred overnight at room temperature. After this time the solvents were removed under vacuum to leave a residue which was purified by column chromatography on silica using dichloromethane/diethyl ether (1:0 to 10:1) to give (E)-1-(4-hydroxy-3-methoxyphenyl)-4,4,6,6-tetramethylhept-1-ene-3,5-dione (177 mg, 92%) as a dark yellow oil: 1H NMR (400 MHz, CDCl3) δ 1.19 (9H, s, C(CH3)3), 1.42 (6H, s, 2×C(CH3)), 3.93 (3H, s, OCH3), 6.03 (1H, brs, phenol OH), 6.54 (1H, d, J=15.6 Hz, vinyl CH), 6.92 (1H, d, J=8.0 Hz, ArH), 6.99 (1H, d, J=2.0 Hz, ArH), 7.12 (1H, dd, J=8.0, 2.0 Hz, ArH), 7.66 (1H, d, J=15.6 Hz, vinyl CH) ppm.

Workup

  1. stirringwas stirred overnight at room temperature
  2. customAfter this time the solvents were removed under vacuum
  3. customto leave a residue which
  4. customwas purified by column chromatography on silica

Sources & evidence

ORD record
ord-14e640f4b4564a02ad96c230c3b4fc05
Source dataset
uspto-grants-2009_09
Patent number
US07589123B2

Reaction notes

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