Triethylamine → HCID 22628477, compound

HRID 278479

Reaction equation

HRID 278479 reaction equation
P(CCCC)(CCCC)CCCC.CCN(CC)CC.[CH2:21]([OH:26])[CH:22]([OH:25])[CH:23]=[CH2:24].Br[C:28]1[CH:29]=[C:30]([CH2:34][C:35]([O:37][CH3:38])=[O:36])[CH:31]=[CH:32][CH:33]=1>CN(C=O)C.O>[OH:26][CH2:21][C:22](=[O:25])[CH2:23][CH2:24][C:32]1[CH:31]=[C:30]([CH2:34][C:35]([O:37][CH3:38])=[O:36])[CH:29]=[CH:28][CH:33]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 103383-Butene-1,2-diolHCID 13831TributylphosphineHCID 11746402Methyl 2-(3-bromophenyl)acetate

Product 1

HCID 22628477HCID 22628477, compoundYield 24.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of Pd (OAc)2 (75 mg, 0.34 mmol), nBu3P (136 mg, 0.67 mmol), and Et3N (442 mg, 4.37 mmol) in DMF (10 ml) was added 3-butene-1,2-diol (296 mg, 3.36 mmol) followed by methyl 3-bromophenylacetate (1.0 g, 4.37 mmol), and the reaction mixture was stirred at 100° C. for 5 h. The reaction mixture was poured into water (100 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 (25 g) column chromatography eluting with toluene/ethyl acetate (20:1) to give methyl 3-(4-hydroxy-3-oxobutyl)phenylacetate (193 mg, 24.4%) as an oil.

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 (25 g) column chromatography
  6. washeluting with toluene/ethyl acetate (20:1)

Sources & evidence

ORD record
ord-083726f3412d4d3c8c9aca3e9842e928
Source dataset
uspto-grants-2002_03
Patent number
US06359145B1

Linked notes

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