Reaktion #72579

Reaktionsgleichung

LiBH4

EtOH

LiBH4

compound

Methyl 6-fluoro-2-oxoindoline-5-carboxylate

EtOH

LiBH4

→

title product

6-Fluoro-5-(hydroxymethyl)indolin-2-one

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirring
2. 2
   Temperaturis maintained for a further 3 hours
3. 3
   workup.STIRRINGthe reaction mixture is stirred overnight
4. 4
   SonstigeThe reaction mixture is quenched with 10 mL of water
5. 5
   workup.ADDITIONsaturated aqueous NH4Cl solution (30 mL) is added
6. 6
   ExtraktionExtraction with EtOAc
7. 7
   Trocknenthe organic phases are dried over Na2SO4
8. 8
   Filtrationfiltered
9. 9
   Sonstigeevaporated in vacuo
10. 10
    SonstigeThe residue obtained
11. 11
    Sonstigeis purified by flash chromatography (DCM/MeOH 10:1)

Vorschrift

A solution of the compound obtained in Step B (2.68 mmoles) in anhydrous THF (20 mL) is maintained under nitrogen in the presence of 0.3 mL of EtOH. The solution is cooled to 0° C. and then 5.28 mmol of LiBH4 are added. The reaction mixture is stirred for 2 hours at ambient temperature; a second portion of LiBH4 (6.20 mmol) is then added and stirring is maintained for a further 3 hours. EtOH (0.3 mL) and a third portion of LiBH4 (9.14 mmol) are added and the reaction mixture is stirred overnight. The reaction mixture is quenched with 10 mL of water, and then saturated aqueous NH4Cl solution (30 mL) is added. Extraction with EtOAc is carried out, and the organic phases are dried over Na2SO4, filtered and evaporated in vacuo. The residue obtained is purified by flash chromatography (DCM/MeOH 10:1) to yield the title product.

Quelle