1,2-Epoxy-3-methoxypropane → 1-methoxy-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propan-2-ol

HRID 417929Notes

Reaction equation

HRID 417929 reaction equation
[NH:1]1[CH:5]=[C:4]([B:6]2[O:14][C:11]([CH3:13])([CH3:12])[C:8]([CH3:10])([CH3:9])[O:7]2)[CH:3]=[N:2]1.[CH3:15][O:16][CH2:17][CH:18]1[O:20][CH2:19]1>>[CH3:15][O:16][CH2:17][CH:18]([OH:20])[CH2:19][N:2]1[CH:3]=[C:4]([B:6]2[O:7][C:8]([CH3:9])([CH3:10])[C:11]([CH3:13])([CH3:12])[O:14]2)[CH:5]=[N:1]1

Participants

3

Reactant 2

HCID 135891,2-Epoxy-3-methoxypropaneHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Product 1

HCID 665837161-methoxy-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propan-2-olYield 108.4%

Conditions

Temperature
98 °C

Procedure

A mixture of 4-pyrazoleboronic acid pinacol ester (4.24 g, 21.9 mmol) and glycidyl methyl ether (7.94 g, 76.6 mmol) was heated to 98° C. for 4 h. It was cooled to r.t. and concentrated in vacuo to give the title compound (6.7 g, quantitative) as a yellow oil. δH (CDCl3) 1.32 (12H, s), 3.37 (3H, s), 3.12-3.54 (3H, m), 4.08-4.37 (3H, m), 7.73 (1H, s), 7.80 (1H, s).

Workup

  1. temperatureIt was cooled to r.t.
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-83ab928ff81d4d2a98b2e9a975f453d8
Source dataset
uspto-grants-2012_01
Patent number
US08093238B2

Reaction notes

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