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With 1H-imidazole; triphenylphosphine on polystyrene; bromine; In dichloromethane; for 16.0h;
A mixture of resin bound triphenyl phosphine (polystyrene 2% cross linking, loading = 3 mmol/g, 3 g, 9 mmol) and imidazole (0.48 g, 7.1 mmol) in DCM (30 ml.) cooled on an ice bath was drop wise added Br2 (1.13 g, 7.1 mmol), whereupon a solution of 4-(2-hydroxy- ethyl)-2-fluoro-1-methoxy-benzene (1.0g, 5.88 mmol) in DCM (5 ml.) was added. The cooling bath was removed and the reaction mixture was stirred for 16 hs before the resin was filtered off. The resin was washed with DCM and the filtrate was concentrated in vacuo. The residue <n="93"/>was purified using column chromatography (SiO2, heptane-EtAOc 95:5) to give 0.82 g of 4- (2-bromo-ethyl)-2-fluoro-1-methoxy-benzene
[4-(2-{4-[2-(3-fluoro-4-methoxy-phenyl)-ethoxy]-phenyl}-ethyl)-2-methyl-4,5-dihydro-oxazol-4-yl]-methanol[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
To a solution of [4- [2- (4-HYDROXYMETHYL-2-METHYL-4, 5-DIHYDRO-OXAZOL-4-YL)-ETHYL]-PHENOL] (300 mg, 1.27 [MMOL)] in dry THF (6 ml) is added under inert atmosphere polystyrene supported triphenylphosphine (loading [3MMOL.] [G',] 1.27 g, 3.81 [MMOL,] 3 eq.), [2- (3-FLUORO-4-METHOXY-] phenyl)-ethanol (647.7 mg, 3.81 mmol, 3 eq. ) and DBAD (877.3 mg, 3.81 mmol, 3 eq. ). The reaction mixture was stirred under inert atmosphere at room temperature overnight. Polystyrene supported triphenylphosphine was then filtered through frit and washed with ethyl acetate and methanol. The reaction mixture was then concentrated to dryness following by addition of 4M HCI in dioxane (3 ml), the reaction was stirred at room temperature for 3 hours. The reaction mixture was quenched by addition of saturated solution of NaHCO3 (10 ml) and ethyl acetate (40 [ML).] The organic layer is separated and the aqueous phase is extracted with ethyl acetate (3 x 40 [ML).] The combined organic extracts are washed with brine, dried over [MGS04,] and evaporated to dryness. Purification using Flashmaster (chexane/ethyl acetate (1/9), ethyl acetate and ethyl acetate/methanol (98/2) ) affords [4- [ (2- {4- [2- (3-FLUORO-4-METHOXY-PHENYL)-ETHOXY]-PHENYL}-ETHYL)-2-METHYL-4, 5-DIHYDRO-OXAZOL-4-] [YL]-METHANOL] as colorless oil. MS [(ESI+)] : 364.2 [(MH+)]
With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 1h;Darkness;
<strong>[452-14-2]2-<strong>[452-14-2](3-fluoro-4-methoxyphenyl)acetic acid</strong></strong> (400 mg, 2.17 mmol) was dissolved in THF (4 mL). The reaction solution was cooled to 0oC. Lithium aluminium hydride (90.8 mg, 2.39 mmol) was added portionwise. The flask was then wrapped with aluminum foil and the resulting solution was stirred for 1 h at room temperature. The reaction was then quenched by the addition of 2 mL of water/ice. The resulting mixture was concentrated under vacuum. The solution was extracted with 2x10 mL of ethyl acetate and the organic layers were combined and evaporated. This afforded 290 mg (78%) of 2-(3-fluoro-4-methoxyphenyl)ethan-1-ol as colorless oil.
2-(3-fluoro-4-methoxyphenyl)acetaldehyde[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
52%
With Dess-Martin periodane; In dichloromethane; at 0 - 20℃; for 2.0h;Inert atmosphere; Darkness;
Into a 100-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed <strong>[404-91-1]2-(3-fluoro-4-methoxyphenyl)ethan-1-ol</strong> (290 mg, 1.70 mmol) in dichloromethane (5 mL). The reaction was cooled to 0oC and Dess-Martin Periodinane (940 mg, 2.22 mmol, 1.30 equiv) was added. The flask was wrapped with aluminum foil and the resulting solution was stirred for 2 h at room temperature. The resulting mixture was concentrated under vacuum. The residue was subjected to FCC eluting with ethyl acetate/petroleum ether (1:5). This afforded the title compound (150 mg, 52%) as a colorless oil. MS: (ES, m/z): 169 [M+H]+.
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