Triethylamine → tert-butyl 4-(2-hydroxyethyl)-1H-pyrazole-1-carboxylate

HRID 1911083Notes

Reaction equation

HRID 1911083 reaction equation
[NH:1]1[CH:5]=[C:4]([CH2:6][CH2:7][OH:8])[CH:3]=[N:2]1.C(N(CC)CC)C.[C:16](=O)([O-:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19]>CN(C)C1C=CN=CC=1.ClCCl>[OH:8][CH2:7][CH2:6][C:4]1[CH:5]=[N:1][N:2]([C:16]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:22])[CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 42936042-(1H-Pyrazol-4-yl)ethanolHCID 4613278tert-Butyl carbonate

Product 1

HCID 54249732tert-butyl 4-(2-hydroxyethyl)-1H-pyrazole-1-carboxylate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

1.10 g (9.81 mmol) 2-(1H-pyrazol-4-yl)-ethanol, 0.20 g (1.64 mmol) 4-dimethylaminopyridine and 1.50 ml (10.3 mmol) triethylamine were placed in 30 ml dichloromethane, the reaction mixture was cooled to 0° C. and 2.20 g (9.88 mmol) tert. butyl carbonate was slowly added. The mixture was stirred for 2 h at ambient temperature and then overnight at ambient temperature. It was diluted with 50 ml dichloromethane and washed with 10% citric acid solution and 15% potassium carbonate solution, the organic phase was dried, filtered and the solvent was eliminated from the filtrate.

Workup

  1. customovernight
  2. customat ambient temperature
  3. washwashed with 10% citric acid solution and 15% potassium carbonate solution
  4. customthe organic phase was dried
  5. filtrationfiltered

Sources & evidence

ORD record
ord-9b3773329892419daa3a344396e63300
Source dataset
uspto-grants-2013_12
Patent number
US08604049B2

Reaction notes

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