Aluminium lithium hydride → (2-(4-Methyl-3-(3-methylbut-2-enyloxy)phenylamino)oxazol-4-yl)methanol

HRID 1474010Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[O:10][CH:11]=[C:12]([C:14](OCC)=[O:15])[N:13]=2)=[CH:4][C:3]=1[O:19][CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[O:10][CH:11]=[C:12]([CH2:14][OH:15])[N:13]=2)=[CH:4][C:3]=1[O:19][CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of the compound ethyl 2-(4-methyl-3-(3-methylbut-2-enyloxy)phenylamino)oxazole-4-carboxylate (42 mg, 0.13 mmol) in anhydro THF (1 mL) was added to a suspension of LiAlH4 (10 mg, 0.25 mmol) in dry THF (1 mL) cooled at 0° C. under nitrogen atmosphere. After 2 h, the reaction mixture was quenched with H2O, filtrated, dried over MgSO4 and concentrated. The title compound was purified by flash chromatography on silica gel (hexane:EtOAc 1/1) to afford the product (13 mg, 34% yield).

Workup

customthe reaction mixture was quenched with H2O
filtrationfiltrated
dry with materialdried over MgSO4
concentrationconcentrated
customThe title compound was purified by flash chromatography on silica gel (hexane:EtOAc 1/1)

Sources & evidence

ORD record: ord-be2b52f770e64ee2a0aab3d2beb22601
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018209B2

Reaction notes

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