3-Fluoro-4-hydroxybenzeneacetic acid → Methyl 2-(3-fluoro-4-hydroxyphenyl)acetate

HRID 453508

Reaktionsgleichung

Reaktionsgleichung von HRID 453508
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8].[Si](C=[N+]=[N-])(C)(C)[CH3:14]>C1COCC1.CO>[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([O:12][CH3:14])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8]

Komponenten

4

Edukt 2

HCID 680143-Fluoro-4-hydroxybenzeneacetic acidHCID 167693Trimethylsilyldiazomethane

Produkt 1

HCID 10797559Methyl 2-(3-fluoro-4-hydroxyphenyl)acetateAusbeute 64,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899815MeOH tetrahydrofuranLösungsmittel

Versuchsvorschrift

2-(3-Fluoro-4-hydroxyphenyl)acetic acid (1.0 g, 5.88 mmol) was diluted with THF:MeOH (3:1) (10 mL) followed by the addition of TMSCHN2 (5.88 ml, 11.8 mmol). After stirring for 1 hour, the reaction was quenched with 2N HCl and diluted with DCM. The layers were separated and the organic layer was dried over MgSO4, filtered and concentrated. The material was purified by silica gel chromatography, eluting with hexanes:ethyl acetate (2:1) to yield methyl 2-(3-fluoro-4-hydroxyphenyl)acetate (700 mg, 64.7% yield) as a clear oil.

Aufarbeitung

  1. customthe reaction was quenched with 2N HCl
  2. additiondiluted with DCM
  3. customThe layers were separated
  4. dry with materialthe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe material was purified by silica gel chromatography
  8. washeluting with hexanes:ethyl acetate (2:1)

Quellen und Nachweise

ORD-Eintrag
ord-7e60a6359e424f16becd7cc037e0ee9c
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492437B2

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