Aluminium lithium hydride → {1-[4-(trifluoromethoxy)phenyl]-1H-pyrazol-4-yl}methanol

HRID 1496929Notes

Reaction equation

[F:1][C:2]([F:21])([F:20])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[C:13]([C:15](OCC)=[O:16])[CH:12]=[N:11]2)=[CH:6][CH:5]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[F:21][C:2]([F:1])([F:20])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[C:13]([CH2:15][OH:16])[CH:12]=[N:11]2)=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of ester 116 (0.730 g, 2.43 mmol) and LiAlH4 (0.200 g, 5.28 mmol) in Et2O (20 mL) was refluxed for 2 h. The mixture was cooled to 0° C., quenched with ice, diluted with Et2O (100 mL) and filtered through Celite. The organic layer was dried (MgSO4), then column chromatography on silica gel (19:1 CH2Cl2:EtOAc) gave {1-[4-(trifluoromethoxy)phenyl]-1H-pyrazol-4-yl}methanol (117) (0.520 g, 83%) as a white solid: mp 73-74° C.; 1H NMR (CDCl3) δ 7.91 (s, 1H), 7.67-7.73 (m, 3H), 7.31 (d, J=8.4 Hz, 2H), 4.69 (d, J=5.5 Hz, 2H), 1.57 (t, J=5.5 Hz, 1H). APCI MS m/z 259 [M+H]+.

Workup

temperaturewas refluxed for 2 h
customquenched with ice
additiondiluted with Et2O (100 mL)
filtrationfiltered through Celite
dry with materialThe organic layer was dried (MgSO4)

Sources & evidence

ORD record: ord-d0512e3ce10844fea26e69edafc74fec
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09198913B2

Reaction notes

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