Triethylamine → HCID 19907458, compound

HRID 2371562Notes

Reaction equation

HRID 2371562 reaction equation
C(N(CC)CC)C.I[C:9]1[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][CH:10]=1.[CH2:20]([OH:24])[CH2:21][C:22]#[CH:23]>[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)(=O)C>[OH:24][CH2:20][CH2:21][C:22]#[C:23][C:9]1[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 135663-Butyn-1-OLHCID 142891Ethyl 4-iodobenzoate

Product 1

HCID 19907458HCID 19907458, compoundYield 100.8%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To 50 ml of triethylamine were added 5.52 g of ethyl p-iodobenzoate, 1.54 g of 3-butyn-1-ol, 41 mg of cuprous iodide and 77 mg of bis(triphenylphosphine) palladium chloride, and the mixture was stirred for 2.5 hours under nitrogen flow. After adding 50 ml of ethyl acetate, the mixture was filtered to remove the precipitate, washed three times with 30 ml of water, dried over magnesium sulfate, and evaporated under a reduced pressure to obtain 4.4 g of ethyl p-(4-hydroxy-1-butynyl)benzoate as a colorless oil.

Workup

  1. filtrationthe mixture was filtered
  2. customto remove the precipitate
  3. washwashed three times with 30 ml of water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under a reduced pressure

Sources & evidence

ORD record
ord-b6bfaf7cd3054dfba918ecea13cc23d6
Source dataset
uspto-grants-1992_03
Patent number
US05093370

Reaction notes

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