Ethylene carbonate → 2-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)ethan-1-ol

HRID 2362655Notes

Reaction equation

HRID 2362655 reaction equation
[CH3:1][C:2]1([CH3:14])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[N:11][NH:12][CH:13]=2)[O:3]1.[O:15]1[CH2:19][CH2:18]OC1=O.C(=O)([O-])[O-].[Cs+].[Cs+].C(=O)([O-])[O-]>C(OCC)(=O)C>[CH3:1][C:2]1([CH3:14])[C:6]([CH3:7])([CH3:8])[O:5][B:4]([C:9]2[CH:13]=[N:12][N:11]([CH2:18][CH2:19][OH:15])[CH:10]=2)[O:3]1

Participants

6

Reactant 4

HCID 7303Ethylene carbonateHCID 10796Cesium carbonateHCID 19660Carbonate IonHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Product 1

HCID 457888552-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)ethan-1-ol

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (9.66 g, 49.8 mmol), 1,3-dioxolan-2-one (21 g, 238 mmol) and cesium carbonate (16 g, 49.1 mmol) were combined in a 100 mL round bottom flask. The reaction was warmed from room temperature to 100° C. in an oil bath, by which time the carbonate had melted and served as the solvent for the reaction, which remained a slurry. After heating for 3.5 hours, the reaction was cooled to room temperature and was diluted with ethyl acetate, then filtered through diatomaceous earth washing repeatedly with ethyl acetate. The filtrate was concentrated, then purified by chromatography on an Analogix® Intelliflash™ purification system using a SF60-200 g column at a flow rate of 80 mL/minute, eluting as follows: 5 minutes at 20% ethyl acetate/hexanes, then ramped from 40% to 90% ethyl acetate/hexanes over 35 minutes, then 100% ethyl acetate for another 20 minutes, to provide the title compound. MS ESI(+) m/z 239.0 (M+H)+.

Workup

  1. customserved as the solvent for the reaction, which
  2. temperatureAfter heating for 3.5 hours
  3. filtrationfiltered through diatomaceous earth
  4. washwashing repeatedly with ethyl acetate
  5. concentrationThe filtrate was concentrated
  6. custompurified by chromatography on an Analogix® Intelliflash™ purification system
  7. washeluting
  8. wait100% ethyl acetate for another 20 minutes

Sources & evidence

ORD record
ord-af88966dd6e54b0787d007ba6dadb9f7
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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