3-Benzyloxybenzaldehyde → 1-(3-(Benzyloxy)phenyl)but-2-yn-1-ol

HRID 1662567

Reaktionsgleichung

[C:1]([Mg]Br)#[C:2][CH3:3].[CH2:6]([O:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH:17]=[O:18])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C1COCC1>[CH2:6]([O:13][C:14]1[CH:15]=[C:16]([CH:17]([OH:18])[C:1]#[C:2][CH3:3])[CH:19]=[CH:20][CH:21]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

A 1 L round bottom flask was charged with 1-propynylmagnesium bromide (0.5 M in THF) (available from Aldrich) (245 mL, 123 mmol) and cooled to −78° C. To the cold slurry was added a solution of 3-benzyloxybenzaldehyde (available from Aldrich) (20.0 g, 94.2 mmol) in THF (30 mL) over 15 minutes. The mixture was stirred for 30 minutes at −78° C., the cooling bath was removed, and stirring was continued for 1 hour at ambient temperature. The reaction was quenched with saturated aqueous ammonium chloride and diluted with EtOAc. The organics were washed with water and brine, dried (MgSO4), and concentrated. The crude product was purified by silica gel flash chromatography (0-30% EtOAc/hexane) to afford 93.A (23.1 g, 97% yield) as a pale yellow oil.

Aufarbeitung

customthe cooling bath was removed
stirringstirring
waitwas continued for 1 hour at ambient temperature
customThe reaction was quenched with saturated aqueous ammonium chloride
additiondiluted with EtOAc
washThe organics were washed with water and brine
dry with materialdried (MgSO4)
concentrationconcentrated
customThe crude product was purified by silica gel flash chromatography (0-30% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag: ord-2f4894906a1b460db637c4867fb09e6e
Quelldatensatz: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08030354B2

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