Tetrahydrofuran → 1-(4-Fluorophenyl)-2-(4-pyridyl)ethanediol
Reaction equation
C([Si](C)(C)O[CH2:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)(C)(C)C.C([N-]C(C)C)(C)C.[Li+].[F:24][C:25]1[CH:32]=[CH:31][C:28]([CH:29]=[O:30])=[CH:27][CH:26]=1.C1C[O:36]CC1>>[F:24][C:25]1[CH:32]=[CH:31][C:28]([C:29]([OH:36])([OH:30])[CH2:7][C:8]2[CH:9]=[CH:10][N:11]=[CH:12][CH:13]=2)=[CH:27][CH:26]=1Participants
5
Procedure
To a stirring solution of 2.0 g (11.2 mmol) 4-(t-butyldimethyl-silyloxy)methyl pyridine in 8 ml of THF at -20° C. was added 14.7 mmol of lithium di-iso-propyl amide in THF. Thirty minutes later 4-fluoro-benzaldehyde (1.66 g, 13.4 mmol) was added at which point the solution was allowed to warm slowly to rt. The reaction was quenched with NH4Cl and extracted with ether to afford the crude protected diol which following concentration was dissolved in THF and treated with 17 ml of a 1 molar solution of tetrabutylammonium fluoride in THF overnight. Standard aqueous workup afforded the crude diol which was further purified by column chromatography (hex/EtOAc) to yield 1.6 g (62%) of the titled material.
Workup
- customThe reaction was quenched with NH4Cl
- extractionextracted with ether
- customto afford the crude protected diol which
- concentrationconcentration
- dissolutionwas dissolved in THF
- additiontreated with 17 ml of a 1 molar solution of tetrabutylammonium fluoride in THF overnight
- customStandard aqueous workup afforded the crude diol which
- customwas further purified by column chromatography (hex/EtOAc)
Sources & evidence
- ORD record
- ord-e913660c81f941609691d8f9c7cc7b7f
- Source dataset
- uspto-grants-1997_08
- Patent number
- US05656644
Reaction notes
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