Tetrahydrofuran → 4-{1-Ethyl-1-[4-(3-hydroxy-3-methylbutyl)-3-methyl-phenyl]propyl}-2-methylphenol

HRID 250173Notes

Reaction equation

HRID 250173 reaction equation
[O:1]([C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]([CH3:31])([OH:30])[CH3:29])=[C:22]([CH3:32])[CH:21]=2)([CH2:18][CH3:19])[CH2:16][CH3:17])=[CH:11][C:10]=1[CH3:33])[Si](C(C)(C)C)(C)C.C1COCC1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>CCOC(C)=O>[CH2:16]([C:15]([C:12]1[CH:13]=[CH:14][C:9]([OH:1])=[C:10]([CH3:33])[CH:11]=1)([C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]([OH:30])([CH3:29])[CH3:31])=[C:22]([CH3:32])[CH:21]=1)[CH2:18][CH3:19])[CH3:17]

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 2724141Tetrabutylammonium FluorideHCID 668913814-(4-{1-[4-(Tert-butyl-dimethylsiloxy)-3-methylphenyl]-1-ethylpropyl}-2-methylphenyl)-2-methylbutan-2-ol

Product 1

HCID 574330374-{1-Ethyl-1-[4-(3-hydroxy-3-methylbutyl)-3-methyl-phenyl]propyl}-2-methylphenolYield 79%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(4-{1-[4-(tert-butyl-dimethylsiloxy)-3-methylphenyl]-1-ethylpropyl}-2-methylphenyl)-2-methylbutan-2-ol (0.25 g, 0.50 mmol) in anhyd THF (1.5 mL) was added a 1.0M solution of TBAF in THF (0.70 mL, 0.70 mmol). After 1.5 h the reaction mixture was diluted with EtOAc (30 mL), washed with satd NH4Cl (20 mL) and brine, then dried (Na2SO4) and concentrated under reduced pressure. The crude material was chromatographed (silica, EtOAc/Hex, 0:100 to 40:60) to yield the title compound (0.14 g, 74%) as a white tacky solid: 1H-NMR (C6D6) δ 7.23-7.28 (2H, m), 7.16-7.22 (2H, m), 7.11 (1H, dd, J=2.3, 8.3), 6.64 (1H, d, J=8.3), 5.39 (1H, br s), 2.66 (2H, m), 2.25 (6H, s), 2.21 (4H, q, J=7.3), 1.62 (2H, m), 1.14 (6H, t, J=7.3).

Workup

  1. washwashed with satd NH4Cl (20 mL) and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe crude material was chromatographed (silica, EtOAc/Hex, 0:100 to 40:60)

Sources & evidence

ORD record
ord-9e52a927f0fa4ce7805a7ced1e5a83e1
Source dataset
uspto-grants-2011_01
Patent number
US07863298B2

Reaction notes

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