Ether, ethyl ethynyl → 1-Ethoxyethene-2-boronic acid pinacol ester

HRID 921020Notes

Reaction equation

HRID 921020 reaction equation
[CH3:1][C:2]1([CH3:9])[C:6]([CH3:8])([CH3:7])[O:5][BH:4][O:3]1.[CH2:10]([O:12][C:13]#[CH:14])[CH3:11]>ClCCl.[Cl-].C1([Zr+2]C2C=CC=C2)C=CC=C1.[Cl-]>[CH2:13]([O:12]/[CH:10]=[CH:11]/[B:4]1[O:5][C:6]([CH3:8])([CH3:7])[C:2]([CH3:9])([CH3:1])[O:3]1)[CH3:14]

Participants

5

Reactant 2

HCID 61239Ether, ethyl ethynylHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolane

Product 1

HCID 219739081-Ethoxyethene-2-boronic acid pinacol esterYield 78.13%

Reagents, catalysts & solvents 2

HCID 178420591HCID 178420591, compoundCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

Di(cyclopenta-2,4-dien-1-yl)zirconium(IV) chloride (0.685 g, 2.344 mmol) was added to a solution of 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (5.0 g, 39.1 mmol) in dichloromethane (15 mL) followed by ethoxyethyne (3.01 g, 43.0 mmol) at 0° C., and the mixture was stirred for 16 h at 25° C. Insoluble solids were filtered off, and filtrate was concentrated. Residue was partitioned between ethyl acetate and water. Organic layer was separated, washed with brine, dried over sodium sulphate, filtered and concentrated in vacuo to afford title compound (6.04 g, 78.13%) as oil. 1H NMR (400 MHz, CDCl3): δ 7.04 (d, J=14.0 Hz, 1H), 4.43 (d, J=14.8 Hz, 1H), 3.84 (q, J=7.2 Hz, 2H), 1.32-1.2 (m, 15H).

Workup

  1. filtrationInsoluble solids were filtered off
  2. concentrationfiltrate was concentrated
  3. customResidue was partitioned between ethyl acetate and water
  4. customOrganic layer was separated
  5. washwashed with brine
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d05f97cbe3344a5790d6b9915e091bfc
Source dataset
uspto-grants-2016_03
Patent number
US09273069B2

Reaction notes

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