Ethyl benzo[d]thiazole-6-carboxylate → 6-(Hydroxymethyl)benzothiazole

HRID 900060

Reaktionsgleichung

Reaktionsgleichung von HRID 900060
[H-].[H-].[H-].[H-].[Li+].[Al+3].[S:7]1[C:11]2[CH:12]=[C:13]([C:16](OCC)=[O:17])[CH:14]=[CH:15][C:10]=2[N:9]=[CH:8]1>C1COCC1>[S:7]1[C:11]2[CH:12]=[C:13]([CH2:16][OH:17])[CH:14]=[CH:15][C:10]=2[N:9]=[CH:8]1

Komponenten

4

Edukt 2

HCID 10512520Ethyl benzo[d]thiazole-6-carboxylateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 178603856-(Hydroxymethyl)benzothiazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a suspension of 76 mg of LiAlH4 in dry THF (20 mL) under N2 was added dropwise and at 0° C. a solution of ester 39 (207 mg, 1 mmol) in dry THF (6.7 ml). After 2 h. the ice bath was removed and the mixture was stirred overnight at room temperature, then cooled to 0° C. The excess of LiAlH4 was destroyed very cautiously by a saturated solution of NH4Cl. The organic layer was removed and the aqueous layer was extracted with EtOAc. The combined organic extracts were dried (Na2CO3) and evaporated, obtaining an orange oil that was purified by column chromatography, eluting with EtOAc/MeOH (90/10). 1H NMR (CD3OD): δ 9.20 (s, 1H), 8.02 (m, 2H), 7.53 (d, 1H, J=8.04 Hz), 4.76 (s, 2H).

Aufarbeitung

  1. customAfter 2 h. the ice bath was removed
  2. temperaturecooled to 0° C
  3. customThe excess of LiAlH4 was destroyed very cautiously by a saturated solution of NH4Cl
  4. customThe organic layer was removed
  5. extractionthe aqueous layer was extracted with EtOAc
  6. dry with materialThe combined organic extracts were dried (Na2CO3)
  7. customevaporated
  8. customobtaining an orange oil that
  9. customwas purified by column chromatography
  10. washeluting with EtOAc/MeOH (90/10)

Quellen und Nachweise

ORD-Eintrag
ord-d555d95b3511477aa6f01661aaf09038
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07358235B2

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