Water → [(2R)-6-iodo-3,4-dihydro-2H-chromen-2-yl]methanol

HRID 47665

Reaktionsgleichung

Reaktionsgleichung von HRID 47665
B.C1COCC1.[I:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[O:14][C@@H:13]([C:18](O)=[O:19])[CH2:12][CH2:11]2.O.C([O-])(O)=O.[Na+]>C1COCC1>[I:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[O:14][C@@H:13]([CH2:18][OH:19])[CH2:12][CH2:11]2

Komponenten

6

Edukt 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 2723981Borane;tetrahydrofuranHCID 9966213(2R)-6-Iodochromane-2-carboxylic acid

Produkt 1

HCID 9943850[(2R)-6-iodo-3,4-dihydro-2H-chromen-2-yl]methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

A solution of borane-THF complex (1M in THF, 23.4 mmol, 1.2 eq) was added dropwise to a solution of (2R)-6-iodo-3,4-dihydro-2H-chromene-2-carboxylic acid (Example 7, 19.5 mmol, 1.0 eq.) in THF (45 mL) at 10° C. The resulting reaction mixture was stirred at 45° C. for 1.5 hours and was then cooled to 10° C. Next, water was added followed by saturated NaHCO3 solution. The resulting two-phase mixture was separated and aqueous phase was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, concentrated to afford the product as a white solid in quantitative yield that was used without further purification.

Aufarbeitung

  1. customThe resulting reaction mixture
  2. temperaturewas then cooled to 10° C
  3. customThe resulting two-phase mixture was separated
  4. extractionaqueous phase was extracted with ethyl acetate
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-4f4291c27ea243a8876f5559000c68b7
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06699860B2

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