Triethylamine → HCID 19907347, compound

HRID 2371564Notes

Reaction equation

HRID 2371564 reaction equation
C(N([CH2:6][CH3:7])CC)C.I[C:9]1[CH:20]=[CH:19][C:12]([CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:11][CH:10]=1>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.C(OCC)(=O)C>[OH:16][CH2:15][CH2:14][CH2:13][CH2:12][C:6]#[C:7][C:9]1[CH:20]=[CH:19][C:12]([CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 554150Methyl 3-(4-iodophenyl)propanoate

Product 1

HCID 19907347HCID 19907347, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To 40 ml of triethylamine were added 3.68 g of methyl p-iododihydrocinnamate, 1.49 g of 5-hexyl-1-ol, 40 ml of cuprous iodide and 77 mg of bis(triphenylphosphine)-palladium chloride, and the mixture was stirred under nitrogen flow for 2.5 hours. After adding 50 ml of ethyl acetate, the mixture was filtered to remove the resulting precipitate, washed three-times with 30 ml of water, dried over magnesium sulfate, and evaporated under a reduced pressure to obtain 4.0 g of methyl p-(6-hydroxy-1-hexynyl)dihydrocinnamate as an oil. 4.0 g of this oil was stirred with 1.2 g of 5% palladium on carbon in 50 ml of methanol under a hydrogen atmosphere to obtain 2.41 g of methyl p-(6-hydroxyhexyl)dihydrocinnamate. To this compound was added 1.0 g of phosphorus tribromide with ice-cooling, and the mixture was heated at 80° C. for 2 hours, poured into 50 ml of ice-water. The mixture was extracted twice with 50 ml of ethyl acetate, dried over magnesium sulfate and evaporated under a reduced pressure to obtain a residue, which was then applied to a silica gel column and eluted with chloroform/hexane (1:1) to obtain 2.1 g of the title compound as a colorless oil.

Workup

  1. filtrationthe mixture was filtered
  2. customto remove the resulting 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-d1e5421327b64fde9641dd3117b0b6d4
Source dataset
uspto-grants-1992_03
Patent number
US05093370

Reaction notes

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