Tetrahydrofuran → HCID 18357901, compound

HRID 428205Notes

Reaction equation

HRID 428205 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:12]=1[OH:13])[CH:8]=[O:9])([CH3:4])([CH3:3])[CH3:2].C1COCC1.C(N(C(C)C)CC)(C)C.[Cl-].[CH3:33][Si:34]([CH3:40])([CH3:39])[CH2:35][CH2:36][O:37][CH3:38]>O>[C:14]([C:11]1[CH:10]=[C:7]([CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:12]=1[O:13][CH2:38][O:37][CH2:36][CH2:35][Si:34]([CH3:40])([CH3:39])[CH3:33])[CH:8]=[O:9])([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehydeHCID 81531DiisopropylethylamineHCID 18357900HCID 18357900, compound

Product 1

HCID 18357901HCID 18357901, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

12.3 g (52 mmol) of 3,5-di-tert-butyl-4-hydroxybenzaldehyde and 100 ml of THF are introduced into a round-bottomed flask. 10 ml (58 mmol) of diisopropylethylamine and 10.3 ml (58 mmol) of 2-trimethylsilylethoxymethane chloride are added successively and the mixture is refluxed for three hours. 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 (3/97% by volume). After evaporation of the solvents, 15.6 g (82%) of the expected product are collected in the form of a colourless oil.

Workup

  1. temperaturethe mixture is refluxed for three hours
  2. extractionextracted with ethyl ether
  3. customthe organic phase is separated out after settling
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customThe residue obtained
  7. customis purified by chromatography on a column of silica
  8. washeluted with a mixture of ethyl acetate and hexane (3/97% by volume)
  9. customAfter evaporation of the solvents, 15.6 g (82%) of the expected product
  10. customare collected in the form of a colourless oil

Sources & evidence

ORD record
ord-188387500aff4aa5941fc93e8d83ff4c
Source dataset
uspto-grants-2001_11
Patent number
US06313162B1

Reaction notes

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