Sodium borohydride → 9-(Hydroxymethyl)-9H-fluorene-2,7-dicarboxylic acid

HRID 888699

Reaktionsgleichung

Reaktionsgleichung von HRID 888699
[CH:1]([CH:3]1[C:15]2[CH:14]=[C:13]([C:16]([OH:18])=[O:17])[CH:12]=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][C:6]([C:19]([OH:21])=[O:20])=[CH:7][CH:8]=2)=[O:2].[BH4-].[Na+]>O.C1COCC1>[OH:2][CH2:1][CH:3]1[C:15]2[CH:14]=[C:13]([C:16]([OH:18])=[O:17])[CH:12]=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][C:6]([C:19]([OH:21])=[O:20])=[CH:7][CH:8]=2

Komponenten

5

Edukt 2

HCID 4311764Sodium borohydrideHCID 587760249-Formyl-9H-fluorene-2,7-dicarboxylic acid

Produkt 1

HCID 669100179-(Hydroxymethyl)-9H-fluorene-2,7-dicarboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A small sample of 9-formyl-2,7-fluorenedicarboxylic acid (5-10 mg) was dissolved in water with a small amount of THF. An excess amount of sodium borohydride was added and allowed to react for two hours. The reaction was quenched with the careful addition of 1 M HCl until acidic. The product was extracted with ethyl acetate, dried over sodium sulfate, filtered and evaporated to dryness. 1H-NMR (CD3OD): δ (ppm) 8.4 (s, 2H, Ar); 8.2 (m, 2H, Ar); 8.0 (m, 2H, Ar); 4.2 (t, 1H, CH); 4.0 (d, 2H, CH2).

Aufarbeitung

  1. customto react for two hours
  2. customThe reaction was quenched with the careful addition of 1 M HCl until acidic
  3. extractionThe product was extracted with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-c00b2f10a82548f1ad5fb82d00e3be02
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08252275B2

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