Triethylamine → HCID 10943998, compound

HRID 583677Notes

Reaction equation

HRID 583677 reaction equation
[OH:1][CH:2]([CH3:5])[CH:3]=[CH2:4].I[C:7]1[CH:17]=[CH:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][CH:8]=1.CCN(CC)CC>CC#N.CCOCC.CC([O-])=O.CC([O-])=O.[Pd+2]>[O:1]=[C:2]([CH3:5])[CH2:3][CH2:4][C:7]1[CH:17]=[CH:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][CH:8]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 117163-Buten-2-olHCID 142891Ethyl 4-iodobenzoate

Product 1

HCID 10943998HCID 10943998, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

3-Hydroxy-1-butene (Aldrich) (2.15 mL, 25 mmol), ethyl 4-iodobenzoate (5.52 g, 20 mmol), Et3N (3.5 mL, 25 mmol) and Pd(OAc)2 (19 mg, 0.08 mmol) were combined in 6 mL CH3CN, sealed in a glass pressure tube and heated at 100° for 3 h. The mixture was cooled, diluted with Et2O, washed with water, 1N NaOH, 5% KHSO4, and brine, dried (MgSO4), and concentrated. Flash chromatography (silica, 10% EtOAc/hexanes) provided 21-1 as a white crystalline solid.

Workup

  1. customsealed in a glass pressure tube
  2. temperatureheated at 100° for 3 h
  3. temperatureThe mixture was cooled
  4. washwashed with water, 1N NaOH, 5% KHSO4, and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8e12bd47c2f445c7b50be47ee2ccad37
Source dataset
uspto-grants-1999_07
Patent number
US05929120

Reaction notes

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