Tetrahydrofuran → HCID 86688730, compound

HRID 1527958Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([CH3:11])[N:8]([CH2:12][C:13]2[CH:18]=[C:17]([Br:19])[CH:16]=[CH:15][C:14]=2[OH:20])[N:7]=1)=[O:5])[CH3:2].[C:21]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:22]=1.[CH:40]1(CO)CCC1.[CH2:46]1[CH2:50]O[CH2:48][CH2:47]1>>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([CH3:11])[N:8]([CH2:12][C:13]2[CH:18]=[C:17]([Br:19])[CH:16]=[CH:15][C:14]=2[O:20][CH2:48][C:47]([CH2:21][CH3:22])([CH3:40])[CH2:46][CH3:50])[N:7]=1)=[O:5])[CH3:2]

Participants

Reactant 4

HCID 8028Tetrahydrofuran

HCID 11776Triphenylphosphine

HCID 78130Cyclobutylcarbinol

HCID 57875600HCID 57875600, compound2×

Product 1

HCID 86688730HCID 86688730, compound

Conditions

Temperature: 100 °C

Procedure

A solution of 1-(5-bromo-2-hydroxy-benzyl)-5-methyl-1H-pyrazole-3-carboxylic acid ethyl ester, 6 (0.1 g, 0.3 mmol), triphenylphosphine (0.155 g, 0.6 mmol), ditert-butylazodicarboxylate (0.14 g, 0.6 mmol) and cyclobutanemethanol (0.06 ml, 0.6 mmol) in a mixture of THF (8 mL) was heated at 100° C. in an Emrys microwave reactor for 20 minutes. The volatiles were removed in vacuo and the crude product was purified on silica to yield 1-[5-bromo-2-(2-ethyl-2-methyl-butoxy)-benzyl]-5-methyl-1H-pyrazole-3-carboxylic acid ethyl ester, 24.

Workup

customThe volatiles were removed in vacuo
customthe crude product was purified on silica

Sources & evidence

ORD record: ord-2892052220da4e8791a9c080f7688797
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090566B2

Reaction notes

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