Ethyl pent-2-yn-1-oate → HCID 11332473, compound

HRID 1969659Notes

Reaction equation

HRID 1969659 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[C:2]#[C:3][CH2:4][CH3:5]>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].C1COCC1.N1C=CC=CC=1>[C:1]([O:7][CH2:8][CH3:9])(=[O:6])/[CH:2]=[CH:3]\[CH2:4][CH3:5]

Participants

5

Reactant 1

HCID 99169Ethyl pent-2-yn-1-oate

Product 1

HCID 11332473HCID 11332473, compoundYield 98.5%

Reagents, catalysts & solvents 3

HCID 131709914Lindlars catalystCatalystHCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a slurry of Lindlar catalyst (0.844 g, 0.396 mmol) in THF (100 mL) and pyridine (10.00 mL) was added ethyl pent-2-ynoate (5.22 mL, 39.6 mmol). The reaction mixture was sparged with hydrogen for about 10 min and an atmosphere of hydrogen was maintained via balloon. After about 15 h the reaction mixture was filtered through a pad of Celite®, diluted with Et2O (30 mL) and washed with saturated aqueous CuSO4 (40 mL), followed by water (40 mL). The organic layer was separated, dried over anhydrous MgSO4, filtered, and concd in vacuo to provide crude (Z)-ethyl pent-2-enoate (5 g, 98%). 1H NMR (DMSO-d6) δ 1.05 (t, 3H), 1.28 (t, 3H), 2.65 (m, 2H), 4.18 (q, 2H), 5.72 (m, 1H), 6.21 (m, 1H).

Workup

  1. customThe reaction mixture was sparged with hydrogen for about 10 min
  2. temperaturean atmosphere of hydrogen was maintained via balloon
  3. filtrationAfter about 15 h the reaction mixture was filtered through a pad of Celite®
  4. additiondiluted with Et2O (30 mL)
  5. washwashed with saturated aqueous CuSO4 (40 mL)
  6. customThe organic layer was separated
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationfiltered

Sources & evidence

ORD record
ord-3ad063d8f2bb48d3b9c7c8ba7a31114b
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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