Aluminium lithium hydride → 3-(3-(Trifluoromethoxy)phenyl)propan-1-ol

HRID 2200576Notes

Reaction equation

[F:1][C:2]([F:15])([F:14])[O:3][C:4]1[CH:5]=[C:6]([C:10]#[C:11][CH2:12][OH:13])[CH:7]=[CH:8][CH:9]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:1][C:2]([F:14])([F:15])[O:3][C:4]1[CH:5]=[C:6]([CH2:10][CH2:11][CH2:12][OH:13])[CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 3-(3-(trifluoromethoxy)phenyl)prop-2-yn-1-ol (0.3 g, 1.39 mmol) in THF (10 mL) was added LAH (63 mg, 1.68 mmol) portionwise at 0° C. The reaction was stirred at 0° C. for 3 h. The reaction was carefully quenched by dropwise addition of ethyl acetate at 0° C. and the mixture was partitioned between ethyl acetate and water. The combined organic layer was dried over sodium sulfate, filtered and concentrated to give a crude product which was purified by column chromatography eluting with ethyl acetate/petroleum ether (1:4 to 1:1) to give 3-(3-(trifluoromethoxy)phenyl)propan-1-ol (0.26 g, 85.2%) as a yellow oil which was used without purification. 1H-NMR (CD3OD) δ 7.37-7.39(d, 1H), 7.31-7.35(m, 1H), 7.15-7.17 (d, 1H), 4.07-4.11(t, 2H), 2.72-2.76(t, 2H), 1.83-1.90(m, 2H).

Workup

customThe reaction was carefully quenched by dropwise addition of ethyl acetate at 0° C.
customthe mixture was partitioned between ethyl acetate and water
dry with materialThe combined organic layer was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customto give a crude product which
customwas purified by column chromatography
washeluting with ethyl acetate/petroleum ether (1:4 to 1:1)

Sources & evidence

ORD record: ord-c5d897f212b9471aa79572a3a4e3a6a0
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09359359B2

Reaction notes

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