Acetonitrile → (2R)-(4E)-5-(5-isopropoxy-3-pyridyl)-4-penten-2-ol

HRID 489760

Reaction equation

HRID 489760 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7](Br)[CH:8]=[N:9][CH:10]=1)([CH3:3])[CH3:2].[CH3:12][C@@H:13]([OH:17])[CH2:14][CH:15]=[CH2:16].C(N(CC)CC)C.C(#N)C>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>[CH:1]([O:4][C:5]1[CH:6]=[C:7](/[CH:16]=[CH:15]/[CH2:14][C@H:13]([OH:17])[CH3:12])[CH:8]=[N:9][CH:10]=1)([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 6999724(2R)-pent-4-en-2-olHCID 105848083-Bromo-5-(propan-2-yloxy)pyridine

Product 1

HCID 12052266(2R)-(4E)-5-(5-isopropoxy-3-pyridyl)-4-penten-2-olYield 85%

Reagents, catalysts & solvents 3

HCID 80271Tri-o-tolylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 5-isopropoxy-3-bromopyridine (10.26 g, 47.50 mmol), (2R)-4-penten-2-ol (4.91 g, 57.00 mmol), palladium(II) acetate (106 mg, 0.47 mmol), tri-o-tolylphosphine (578 mg, 1.90 mmol), triethylamine (28.46 mL, 204.25 mmol), and acetonitrile (30 mL) were heated in a sealed glass tube at 140° C. for 14 h. The reaction mixture was cooled to ambient temperature, diluted with water, and extracted with chloroform (3×200 mL). The combined chloroform extracts were dried over sodium sulfate, filtered, and concentrated by rotary evaporation to give a pale-yellow oil (8.92 g, 85.0%).

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. extractionextracted with chloroform (3×200 mL)
  3. dry with materialThe combined chloroform extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-21e1597ed67640e8b75bfa8ca218c7f5
Source dataset
uspto-grants-2005_12
Patent number
US06979695B2

Linked notes

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