Triethylamine → HCID 67665375, compound

HRID 1957697Notes

Reaction equation

HRID 1957697 reaction equation
C([CH:3]([O:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][OH:17])=[CH:12][C:11]=1[C:18]12[CH2:27][CH:22]3[CH2:23][CH:24]([CH2:26][CH:20]([CH2:21]3)[CH2:19]1)[CH2:25]2)[CH2:4][O:5][CH3:6])#C.I[C:29]1[CH:38]=[CH:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:31][CH:30]=1.[CH2:39](N(CC)CC)[CH3:40]>O.C(OCC)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Cu](I)I>[OH:17][CH:16]([C:13]1[CH:14]=[CH:15][C:10]([O:9][CH2:8][O:7][CH2:3][CH2:4][O:5][CH3:6])=[C:11]([C:18]23[CH2:25][CH:24]4[CH2:23][CH:22]([CH2:21][CH:20]([CH2:26]4)[CH2:19]2)[CH2:27]3)[CH:12]=1)[C:39]#[C:40][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 131720776HCID 131720776, compound

Product 1

HCID 67665375HCID 67665375, compound

Reagents, catalysts & solvents 4

HCID 83717Copper iodideCatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

2.5 g (6.7 mmol) of a-ethynyl-3-(1-adamantyl)-4-methoxyethoxymethoxyphenylmethanol, 1.2 g (6.7 mmol) of methyl 4-iodobenzoate and 50 ml of triethylamine were introduced into a three-necked flask. The reaction medium was degassed with nitrogen for 30 min, then 380 mg (0.5 mmol) of bis(triphenylphosphine)palladium (II) chloride and 190 mg (0.8 mmol) of copper iodide were successively added. The reaction medium was stirred at room temperature for four hours and was 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 a mixture of ethyl acetate and heptane (20/80). 2.7 g (79%) of methyl 4-[[3-hydroxy-3-[3-(1-adamantyl)-4-methoxyethoxymethoxyphenyl]-1-propynyl]]benzoate, having a melting point of 95°-6° C., were recovered.

Workup

  1. customThe reaction medium was degassed with nitrogen for 30 min
  2. customwas then evaporated to dryness
  3. customthe residue obtained
  4. customThe organic phase was separated out
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe residue obtained
  8. customwas purified by chromatography on a column of silica
  9. washeluted with a mixture of ethyl acetate and heptane (20/80)
  10. customwere recovered

Sources & evidence

ORD record
ord-1056fe1c62d7418dbb8943478f4c4c22
Source dataset
uspto-grants-1998_07
Patent number
US05786379

Reaction notes

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