HCID 57299675, compound → HCID 53823678, compound

HRID 1416977Notes

Reaction equation

[CH3:1][Li].[CH2:3]([O:7][C:8]1[C:13]([CH:14]=[O:15])=[CH:12][C:11]([C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)=[C:10]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)[N:9]=1)[CH2:4][CH2:5][CH3:6]>C1COCC1>[CH2:3]([O:7][C:8]1[C:13]([CH:14]([CH3:1])[OH:15])=[CH:12][C:11]([C:16]2[CH:17]=[CH:18][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:20][CH:21]=2)=[C:10]([C:26]2[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=2)[N:9]=1)[CH2:4][CH2:5][CH3:6]

Participants

Conditions

Temperature: -75 °C

Procedure

Methyl lithium (0.67 ml, 1.5M in diethyl ether, 1.02 mMol) was added by syringe to a stirring solution of 2-butoxy-6-(4-fluorophenyl)-5-[4-(methylsulfonyl)phenyl]pyridine-3-carboxaldehyde [Example 30](0.38 g, 0.88 mMol) in 50 mL THF cooled to -75° C. The cold bath was removed and the reaction mixture was allowed to come to room temperature. Acetic acid (10%, 5 ml) was added. After stirring for 30 minutes, the layers were separated. The organic layer was washed with 50 ml water, dried over sodium sulfate, filtered and concentrated to an oil. The titled material was purified by silica gel chromatography and recrystallized from ethyl acetate-hexane. Anal. Calc'd. C24H26NO4SF; C, 64.99; H, 5.91; N, 3.16. Found: C, 64.96; H, 6.07; N, 3.07.

Workup

customThe cold bath was removed
customto come to room temperature
additionAcetic acid (10%, 5 ml) was added
customthe layers were separated
washThe organic layer was washed with 50 ml water
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated to an oil
customThe titled material was purified by silica gel chromatography
customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record: ord-8c4b3b7c993d4fcfb2ff40996ce619e4
Source dataset: uspto-grants-1999_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05916905

Reaction notes

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