Triethylamine → methyl (4E)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pent-4-enoate

HRID 1482237Notes

Reaction equation

HRID 1482237 reaction equation
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][CH2:3][C:4]#[CH:5].[CH3:9][C:10]1([CH3:17])[C:14]([CH3:16])([CH3:15])[O:13][BH:12][O:11]1.C(N(CC)CC)C>C(OCC)C.[H-].[Cl-].[CH-]1C=CC=C1.[CH-]1C=CC=C1.[Zr+2]>[CH3:9][C:10]1([CH3:17])[C:14]([CH3:16])([CH3:15])[O:13][B:12](/[CH:5]=[CH:4]/[CH2:3][CH2:2][C:1]([O:7][CH3:8])=[O:6])[O:11]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 543061Methyl 4-pentynoateHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolane

Product 1

HCID 89668575methyl (4E)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pent-4-enoateYield 50.1%

Reagents, catalysts & solvents 2

HCID 131718033Bis(cyclopenta-1,3-diene);hydride;zirconium(2+);chlorideCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
65 °C

Procedure

Methyl pent-4-ynoate (5.0 g, 44.6 mmol) and 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (7.42 g, 58.0 mmol) were mixed, zirconocene chloride hydride (1.18 g, 4.46 mmol) and triethylamine (0.622 ml, 4.46 mmol) were added and the mixture was stirred at 65° C. overnight. The reaction solution was left to cool and then diluted with diethyl ether, and the precipitated white solid was removed by filtration through celite. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by column chromatography (hexane:ethyl acetate) to afford the title compound (5.36 g, 50.1%).

Workup

  1. waitThe reaction solution was left
  2. temperatureto cool
  3. customthe precipitated white solid was removed by filtration through celite
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe resulting residue was purified by column chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-c0270252c5a64241b32be66150756907
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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