Tetrahydrofuran → 1-(4-Fluorophenyl)-2-(4-pyridyl)ethanediol

HRID 2293491Notes

Reaction equation

[Si](O[CH2:9][C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1)(C(C)(C)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])[CH2:9][C:10]2[CH:11]=[CH:12][N:13]=[CH:14][CH:15]=2)=[CH:27][CH:26]=1

Participants

Reactant 4

HCID 8028Tetrahydrofuran2×

HCID 680234-Fluorobenzaldehyde

HCID 2724682Lithium diisopropylamide

HCID 109878804-(Tert-butyldimethylsilyloxymethyl)pyridine

Product 1

HCID 187715021-(4-Fluorophenyl)-2-(4-pyridyl)ethanediolYield 62%

Procedure

To a sting solution of 2.0 g (11.2 mmol) 4-(t-butyldimethylsilyloxy)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-fluorobenzaldehyde (1.66 g, 13.4 mmol) was added at which point the solution was allowed to warm slowly to ft. 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

temperatureto warm slowly
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-cb19e5aa8a3c42fe9f66d4b927b4ffa5
Source dataset: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05686455

Reaction notes

Loading…