6-(4-(Trifluoromethyl)phenyl)picolinaldehyde → 1-{6-[4-(Trifluoromethyl)phenyl]-2-pyridinyl}-1-hexanol

HRID 1391759Notes

Reaction equation

[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[C:13]([CH:15]=[O:16])[CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[CH2:19]([Mg]Br)[CH2:20][CH2:21][CH2:22][CH3:23]>C1(C)C=CC=CC=1.CCOCC>[F:18][C:2]([F:17])([F:1])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:14]=[C:13]([CH:15]([OH:16])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH:12]=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 6-[4-(trifluoromethyl)phenyl]-2-pyridinecarbaldehyde (300 mg, 1.19 mmol) in dry toluene (12 mL) under nitrogen was cooled to 0° C. (ice/water bath) and treated with n-pentylmagnesium bromide (0.66 mL of a 2M solution in Et2O, 1.31 mmol) and the resulting mixture was stirred at 0° C. for 2 hours. The reaction was then quenched by the cautious addition of aqueous HCl (2M, 2 mL) and the solvent was removed under vacuum and the residue partitioned between EtOAc (2×50 mL) and aqueous HCl (2M, 50 mL). The organic solution was washed with water (60 mL) then brine (60 mL), dried (MgSO4) and reduced. Purification by SPE (silica, 20 g cartridge) eluting with cyclohexane:EtOAc (gradient 99:1 to 19:1) afforded the title compound as a colourless oil (131 mg).

Workup

customThe reaction was then quenched by the cautious addition of aqueous HCl (2M, 2 mL)
customthe solvent was removed under vacuum
customthe residue partitioned between EtOAc (2×50 mL) and aqueous HCl (2M, 50 mL)
washThe organic solution was washed with water (60 mL)
dry with materialbrine (60 mL), dried (MgSO4)
customPurification by SPE (silica, 20 g cartridge)
washeluting with cyclohexane

Sources & evidence

ORD record: ord-b1ed517e2b3746a7a319d7db2efdd310
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07338960B2

Reaction notes

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