Triethylamine → HCID 67663021, compound

HRID 1957705Notes

Reaction equation

HRID 1957705 reaction equation
[C:1]([CH:3]([C:5]1[CH:10]=[C:9]([C:11]23[CH2:20][CH:15]4[CH2:16][CH:17]([CH2:19][CH:13]([CH2:14]4)[CH2:12]2)[CH2:18]3)[C:8]([O:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH3:27])=[CH:7][C:6]=1[O:28][CH2:29][O:30][CH2:31][CH2:32][O:33][CH3:34])[OH:4])#[CH:2].I[C:36]1[CH:45]=[CH:44][C:39]([C:40]([O:42][CH3:43])=[O:41])=[CH:38][CH:37]=1.C(N(CC)CC)C>O.C(OCC)C>[OH:4][CH:3]([C:5]1[CH:10]=[C:9]([C:11]23[CH2:20][CH:15]4[CH2:14][CH:13]([CH2:19][CH:17]([CH2:16]4)[CH2:18]2)[CH2:12]3)[C:8]([O:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH3:27])=[CH:7][C:6]=1[O:28][CH2:29][O:30][CH2:31][CH2:32][O:33][CH3:34])[C:1]#[C:2][C:36]1[CH:45]=[CH:44][C:39]([C:40]([O:42][CH3:43])=[O:41])=[CH:38][CH:37]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 69273Methyl 4-iodobenzoateHCID 19068251HCID 19068251, compound

Product 1

HCID 67663021HCID 67663021, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

760 mg (1.6 mmol) of a-ethynyl-5-(1-adamantyl)-2,4-di(methoxyethoxymethoxy)benzenemethanol, 420 mg (1.6 mmol) of methyl 4-iodobenzoate and 20 ml of triethylamine were introduced into a three-necked flask. The reaction medium was degassed with nitrogen for 30 min, then 90 mg of bis(triphenylphosphine)palladium(II) chloride and 37 mg of copper iodide were added successively. The reaction medium was stirred at room temperature for four hours, then evaporated to dryness, and the residue obtained was taken up in water and ethyl ether. The organic phase was separated out after settling had taken place, dried over magnesium sulfate and evaporated. The residue obtained was purified by chromatography on a column of silica, eluted with dichloromethane and 800 mg (82%) of the expected methyl ester were recovered in the form of a brown oil.

Workup

  1. customThe reaction medium was degassed with nitrogen for 30 min
  2. addition90 mg of bis(triphenylphosphine)palladium(II) chloride and 37 mg of copper iodide were added successively
  3. customevaporated to dryness
  4. customthe residue obtained
  5. customThe organic phase was separated out
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customThe residue obtained
  9. customwas purified by chromatography on a column of silica
  10. washeluted with dichloromethane and 800 mg (82%) of the expected methyl ester
  11. customwere recovered in the form of a brown oil

Sources & evidence

ORD record
ord-b27bd23d657744b4b4eb8e92e467d6d2
Source dataset
uspto-grants-1998_07
Patent number
US05786379

Reaction notes

Loading…