Tetrabutylammonium Fluoride → 2-(4-Tert-butoxyphenoxy)ethanol

HRID 513177Notes

Reaction equation

HRID 513177 reaction equation
[C:1]([O:5][C:6]1[CH:22]=[CH:21][C:9]([O:10][CH2:11][CH2:12][O:13][Si](C(C)(C)C)(C)C)=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>CC1OCCC1.C1COCC1>[C:1]([O:5][C:6]1[CH:22]=[CH:21][C:9]([O:10][CH2:11][CH2:12][OH:13])=[CH:8][CH:7]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86720567[2-(4-Tert-butoxyphenoxy)ethoxy](tert-butyl)dimethylsilane

Product 1

HCID 712301312-(4-Tert-butoxyphenoxy)ethanolYield 93%

Reagents, catalysts & solvents 2

HCID 73012-MethyltetrahydrofuranSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

[2-(4-Tert-butoxyphenoxy)ethoxy](tert-butyl)dimethylsilane (1.7 g, 5.24 mmole) was taken up in 2-MeTHF (10 mL). To this was added 1M TBAF (16 mL, 16.00 mmole) in THF then the mixture was heated to 60° C. After 4 hr the mixture was cooled to RT and concentrated. The residue was taken up in H2O and extracted with CH2Cl2 (3×). The combined organic layers were dried (MgSO4), filtered, and concentrated. Flash column chromatography (Biotage-SNAP-50 g SiO2, 30% EtOAc/hexanes) gave the title compound (1.02 g, 93%) as a clear oil. 1H NMR (400 MHz, CDCl3): δ 6.94-6.90 (m, 2 H); 6.83-6.79 (m, 2 H); 4.07-4.02 (m, 2 H); 3.97-3.91 (m, 2 H); 1.30 (s, 9 H).

Workup

  1. temperatureAfter 4 hr the mixture was cooled to RT
  2. concentrationconcentrated
  3. extractionextracted with CH2Cl2 (3×)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c9c3780323f74043abec7b8fd18e1b92
Source dataset
uspto-grants-2015_08
Patent number
US09102673B2

Reaction notes

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