Triethylamine → (2S)-(4E)-5-(5-Isopropoxy-3-pyridyl)-4-penten-2-ol

HRID 1828928Notes

Reaction equation

HRID 1828928 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:8][CH:9]([CH3:11])[CH3:10])[CH:5]=[N:6][CH:7]=1.[CH3:12][C@H:13]([OH:17])[CH2:14][CH:15]=[CH2:16].C(N(CC)CC)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(#N)C>[CH:9]([O:8][C:4]1[CH:3]=[C:2](/[CH:16]=[CH:15]/[CH2:14][C@@H:13]([OH:17])[CH3:12])[CH:7]=[N:6][CH:5]=1)([CH3:11])[CH3:10]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 6994332(S)-(+)-4-Penten-2-olHCID 105848083-Bromo-5-(propan-2-yloxy)pyridine

Product 1

HCID 68477280(2S)-(4E)-5-(5-Isopropoxy-3-pyridyl)-4-penten-2-olYield 60.7%

Reagents, catalysts & solvents 3

HCID 80271Tri-o-tolylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of 5-bromo-3-isopropoxypyridine (12.56 g, 58.13 mmol), (2S)-4-penten-2-ol (5.00 g, 58.05 mmol), palladium(II) acetate (130 mg, 0.58 mmol), tri-o-tolylphosphine (706 mg, 2.32 mmol), triethylamine (35 mL, 252 mmol) and acetonitrile (35 mL) was heated in a sealed glass tube at 130–140° C. for 8 h. The reaction mixture was cooled to ambient temperature. The solvent was removed under reduced pressure on a rotary evaporator. Water (50 mL) was added and the mixture was extracted with chloroform (3×50 mL). The combined chloroform extracts were dried (K2CO3), filtered, and concentrated by rotary evaporation. The crude product was purified by column chromatography over silica gel, eluting with chloroform-acetone (95:5, v/v). Selected fractions were combined and concentrated by rotary evaporation, producing 7.80 g (60.7%) of a pale-yellow oil.

Workup

  1. temperaturewas heated in a sealed glass tube at 130–140° C. for 8 h
  2. customThe solvent was removed under reduced pressure on a rotary evaporator
  3. additionWater (50 mL) was added
  4. extractionthe mixture was extracted with chloroform (3×50 mL)
  5. dry with materialThe combined chloroform extracts were dried (K2CO3)
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation
  8. customThe crude product was purified by column chromatography over silica gel
  9. washeluting with chloroform-acetone (95:5
  10. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-0b9980dd54594f839dbcbc8c44d9264b
Source dataset
uspto-grants-2006_06
Patent number
US07060826B2

Reaction notes

Loading…