Tetrahydrofuran → HCID 17867292, compound

HRID 428207Notes

Reaction equation

HRID 428207 reaction equation
C[Si](C)(C)C#C[C:5]1[C:10]([C:11]([CH3:14])([CH3:13])[CH3:12])=[C:9]([O:15][CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[C:8]([C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:7][C:6]=1[CH2:28][OH:29].[CH2:32]1COC[CH2:33]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O>[C:32]([CH:28]([C:6]1[CH:5]=[C:10]([C:11]([CH3:13])([CH3:14])[CH3:12])[C:9]([O:15][CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:21])([CH3:23])[CH3:22])=[C:8]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH:7]=1)[OH:29])#[CH:33]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 131722969HCID 131722969, compound

Product 1

HCID 17867292HCID 17867292, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

18.5 g (40 mmol) of α-trimethylsilylethynyl-3,5-di-tert-butyl-4-(2-trimethylsilylethoxymethoxy)benzenemethanol and 50 ml of THF are introduced into a round-bottomed flask and 40 ml (44 mmol) of tetrabutylammonium fluoride solution (1.1 M in THF) are added dropwise. The mixture is stirred at room temperature for one hour, the reaction medium is poured into water and extracted with ethyl ether and the organic phase is separated out after settling has taken place, dried over magnesium sulphate and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a mixture of ethyl acetate and hexane (5/95 by volume). After evaporation of the solvents, 13.5 g (86%) of α-ethynyl-3,5-di-tert-butyl-4-(2-trimethylsilylethoxymethoxy)benzenemethanol are collected in the form of a colourless oil.

Workup

  1. extractionextracted with ethyl ether
  2. customthe organic phase is separated out after settling
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customThe residue obtained
  6. customis purified by chromatography on a column of silica
  7. washeluted with a mixture of ethyl acetate and hexane (5/95 by volume)
  8. customAfter evaporation of the solvents, 13.5 g (86%) of α-ethynyl-3,5-di-tert-butyl-4-(2-trimethylsilylethoxymethoxy)benzenemethanol
  9. customare collected in the form of a colourless oil

Sources & evidence

ORD record
ord-bc47075c41e245b78c7502325ad6a65d
Source dataset
uspto-grants-2001_11
Patent number
US06313162B1

Reaction notes

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