Tetrahydrofuran → HCID 22171050, compound

HRID 2376241Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[N:12]=[C:11]([CH2:22][CH:23]([C:27]3[CH:28]=[C:29]([CH3:33])[CH:30]=[CH:31][CH:32]=3)[C:24](O)=[O:25])[CH:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].O1CCCC1.[H-].C([Al+]CC(C)C)C(C)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C(OCC)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]([C:14]3[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=3)[N:12]=[C:11]([CH2:22][CH:23]([C:27]3[CH:28]=[C:29]([CH3:33])[CH:30]=[CH:31][CH:32]=3)[CH2:24][OH:25])[CH:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

Conditions

Temperature: -78 °C

Procedure

To a 3-neck round-bottom flask charged with nitrogen was added 3-[5-(3,4-dichloro-phenyl)-1-(4-methoxy-phenyl)-1H-pyrazol-3-yl]-2-m-tolyl-propionic acid ethyl ester (see Method 2, product before hydrolysis; 798 mg, 1.57 mmol, 1.0 equiv) and tetrahydrofuran (6.0 mL). The mixture was cooled to -78° C., then diisobutyl aluminum hydride (4.7 mL, 1.0 M solution in tetrahydrofuran) was added dropwise. The reaction mixture was stirred at −78° C. for 30 min then allowed to warm to room temperature and stirred 1 h. The mixture was then poured slowly into a satd aq solution of Rochelle salt (50 mL). Diethyl ether (50 mL) was added, and the resulting mixture was stirred for 3 h. The organic layer was dried (Na2SO4) and concentrated under reduced pressure to afford 732 mg of the desired alcohol, which was used in the next step without purification.

Workup

additionTo a 3-neck round-bottom flask charged with nitrogen
temperatureto warm to room temperature
stirringstirred 1 h
stirringthe resulting mixture was stirred for 3 h
dry with materialThe organic layer was dried (Na2SO4)
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-64fc4c42dcdf4c64af3498053b19c2c8
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07465808B2

Reaction notes

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