Triethylamine → HCID 22628483, compound

HRID 278477

Reaction equation

HRID 278477 reaction equation
P(CCCC)(CCCC)CCCC.CCN(CC)CC.[CH2:21]([OH:26])[CH:22]([OH:25])[CH:23]=[CH2:24].I[C:28]1[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=1>CN(C=O)C.O>[OH:26][CH2:21][C:22](=[O:25])[CH2:23][CH2:24][C:28]1[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 103383-Butene-1,2-diolHCID 122074-IodotolueneHCID 13831Tributylphosphine

Product 1

HCID 22628483HCID 22628483, compoundYield 73.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of Pd (OAc)2 (40 mg, 0.18 mmol), nBu3P (71 mg, 0.35 mmol), and Et3N (232 mg, 2.29 mmol) in DMF (5 ml) was added 3-butene-1,2-diol (155 mg, 1.76 mmol) followed by 4-iodotoluene (500 mg, 2.29 mmol), and the reaction mixture was stirred at 100° C. for 1.5 h. The reaction mixture was poured into water (50 ml) and extracted with ethyl acetate. The organic layer was washed with brine, dried (magnesium sulfate) and evaporated in vacuo. The residue was purified by silica gel (10 g) column chromatography eluting with toluene/ethyl acetate (50:1) to give 1-hydroxy-4-(p-tolyl)butan-2-one (230 mg, 73.4%) as a pale yellow solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried (magnesium sulfate)
  4. customevaporated in vacuo
  5. customThe residue was purified by silica gel (10 g) column chromatography
  6. washeluting with toluene/ethyl acetate (50:1)

Sources & evidence

ORD record
ord-5ddef9eff4e543c39820720f77525efe
Source dataset
uspto-grants-2002_03
Patent number
US06359145B1

Linked notes

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