Sodium Hydroxide → (4'-Fluorospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-4'-yl)methanol

HRID 2040299Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2040299
[F:1][C:2]1([C:16](OCC)=[O:17])[CH2:7][CH2:6][C:5]2([O:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[O:8]2)[CH2:4][CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1.C(OCC)(=O)C>[F:1][C:2]1([CH2:16][OH:17])[CH2:3][CH2:4][C:5]2([O:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[O:11]2)[CH2:6][CH2:7]1

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 67126734Ethyl 4'-fluorospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-4'-carboxylate

Produkt 1

HCID 67126697(4'-Fluorospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-4'-yl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of EXAMPLE 350B (23 g) in tetrahydrofuran (150 mL) was added lithium aluminum hydride (3.11 g). The mixture was stirred overnight. Aqueous 2N NaOH solution was added dropwise to the reaction mixture. The mixture was then diluted with ethyl acetate (600 mL) and washed with water, brine and dried over Na2SO4. Filtration and evaporation of the solvent gave the crude product which was loaded on a 600 g analogics column and eluted with 10% to 20% ethyl acetate in hexane to provide the title compound.

Aufarbeitung

  1. washwashed with water, brine
  2. dry with materialdried over Na2SO4
  3. filtrationFiltration and evaporation of the solvent
  4. customgave the crude product which
  5. washeluted with 10% to 20% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-6817c15c175a4daf9fb8f2184049a391
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08580794B2

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