Tetrabutylammonium Fluoride → ethyl 5-(3-hydroxypropyl)-1H-pyrazole-3-carboxylate

HRID 2298216Notes

Reaction equation

HRID 2298216 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([CH2:11][CH2:12][CH2:13][O:14][Si](C(C)(C)C)(C)C)[NH:8][N:7]=1)=[O:5])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([CH2:11][CH2:12][CH2:13][OH:14])[NH:8][N:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 539527935-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-1H-pyrazole-3-carboxylic Acid Ethyl Ester

Product 1

HCID 54511322ethyl 5-(3-hydroxypropyl)-1H-pyrazole-3-carboxylateYield 79.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-1H-pyrazole-3-carboxylic Acid ethyl ester (327 mg, 1.05 mmol) and tetrabutylammonium fluoride (288 mg, 1.10 mmol) in THF (50 mL) was stirred at room temperature for 1 h. The reaction mixture was concentrated in vacuo. Flash chromatography (EtOAc to EtOAc:MeOH 19:1) provided the title alcohol (165 mg). 1H NMR (400 MHz, CDCl3) δ 6.58 (s, 1H), 4.35 (q, 2H), 3.71 (t, 2H), 2.84 (t, 2H), 1.91 (m, 2H), 1.36 (t, 3H); MS 199 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-476ca429a2aa45d6b7aa52244907c096
Source dataset
uspto-grants-2002_12
Patent number
US06492412B2

Reaction notes

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