Triethylamine → HCID 18357929, compound

HRID 428208Notes

Reaction equation

HRID 428208 reaction equation
[C:1]([CH:3]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:8]([O:15][CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])=[C:7]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH:6]=1)[OH:4])#[CH:2].I[C:29]1[CH:38]=[CH:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:31][CH:30]=1.C(N(CC)CC)C>O.C(OCC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](I)I>[OH:4][CH:3]([C:5]1[CH:6]=[C:7]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:8]([O:15][CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:21])([CH3:23])[CH3:22])=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)[C:1]#[C:2][C:29]1[CH:38]=[CH:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:31][CH:30]=1

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 69273Methyl 4-iodobenzoateHCID 17867292HCID 17867292, compound

Product 1

HCID 18357929HCID 18357929, compound

Reagents, catalysts & solvents 4

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

6 g (15.4 mmol) of α-ethynyl-3,5-di-tert-butyl-4-(2-trimethylsilylethoxymethoxy)benzenemethanol, 4.1 g (15.4 mmol) of methyl 4-iodobenzoate and 50 ml of triethylamine are introduced into a three-necked flask. The reaction medium is degassed with nitrogen for 30 minutes and 820 mg (1.2 mmol) of bis(triphenylphosphine)palladium(II) chloride and 360 mg (1.9 mmol) of copper iodide are then added successively. The reaction medium is stirred at room temperature for four hours and evaporated to dryness, and the residue obtained is taken up in water and ethyl ether. The organic phase is separated out after settling has taken place, dried over magnesium sulphate and then evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a mixture of dichloromethane and heptane (80/20% by volume); 6.7 g (84%) of methyl 4-{3-hydroxy-3-[3,5-di-tert-butyl-4-(2-trimethylsilylethoxymethoxy)phenyl]-1-propynyl}benzoate are collected, with a melting point of 91-2° C.

Workup

  1. customThe reaction medium is degassed with nitrogen for 30 minutes
  2. customevaporated to dryness
  3. customthe residue obtained
  4. customThe organic phase is separated out after settling
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customThe residue obtained
  8. customis purified by chromatography on a column of silica
  9. washeluted with a mixture of dichloromethane and heptane (80/20% by volume)
  10. custom6.7 g (84%) of methyl 4-{3-hydroxy-3-[3,5-di-tert-butyl-4-(2-trimethylsilylethoxymethoxy)phenyl]-1-propynyl}benzoate are collected, with a melting point of 91-2° C.

Sources & evidence

ORD record
ord-467cbbbe2adc4a71b37bad130de5930a
Source dataset
uspto-grants-2001_11
Patent number
US06313162B1

Reaction notes

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