Methanol → Methyl 2-(2-fluoro-4-methoxyphenyl)acetate

HRID 604663Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 604663
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH2:10][C:11]([OH:13])=[O:12].CO.[Si](C=[N+]=[N-])(C)(C)[CH3:17]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH2:10][C:11]([O:13][CH3:17])=[O:12]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 167693TrimethylsilyldiazomethaneHCID 193619782-(2-Fluoro-4-methoxyphenyl)acetic acid

Produkt 1

HCID 21472203Methyl 2-(2-fluoro-4-methoxyphenyl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of (2-fluoro-4-methoxyphenyl)acetic acid (500 mg, 2.72 mmol) in toluene (20 mL) was added MeOH (3 mL) and TMS diazomethane (2.04 mL of a 2M solution in hexanes, 4.08 mmol). After 15 min, the reaction was quenched by the addition of HOAc (250 μL). The reaction was diluted with EtOAc (100 mL) and washed with saturated NaHCO3 (2×25 mL) and brine (25 mL). The organic layer was dried (Na2SO4), filtered and concentrated. Purification of the residue by flash chromatography (0 to 25% EtOAc/hexanes) afforded methyl (2-fluoro-4-methoxyphenyl)acetate. 1H NMR (500 MHz, CDCl3): δ 7.15 (t, J=8.6 Hz, 1H), 6.62-6.68 (m, 2H), 3.78 (s, 3H), 3.70 (s, 3H), 3.60 (s, 2H).

Aufarbeitung

  1. customthe reaction was quenched by the addition of HOAc (250 μL)
  2. additionThe reaction was diluted with EtOAc (100 mL)
  3. washwashed with saturated NaHCO3 (2×25 mL) and brine (25 mL)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification of the residue by flash chromatography (0 to 25% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-6df4557615804591b33a204f8a249f4c
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07910592B2

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