Boron trifluoride etherate → Methyl I(2)-[(4-hydroxyphenyl)methyl]-5-methyl-2-thiazolepropanoate

HRID 1816001Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1816001
[CH3:1][C:2]1[S:6][C:5]([CH:7]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20]CC3C=CC=CC=3)=[CH:16][CH:15]=2)[CH2:8][C:9]([O:11][CH3:12])=[O:10])=[N:4][CH:3]=1.B(F)(F)F.CCOCC>CCS>[CH3:1][C:2]1[S:6][C:5]([CH:7]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[CH2:8][C:9]([O:11][CH3:12])=[O:10])=[N:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 8000Boron trifluoride etherateHCID 86759662Methyl (+/-)-3-(5-methylthiazol-2-yl)-4-(4-benzyloxyphenyl)butanoate

Produkt 1

HCID 20775669Methyl I(2)-[(4-hydroxyphenyl)methyl]-5-methyl-2-thiazolepropanoateAusbeute 86,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6343EthanethiolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of methyl (±)-3-(5-methylthiazol-2-yl)-4-(4-benzyloxyphenyl)butanoate (0.99 mmole, crude) in EtSH (5 mL) at RT was added BF3 OEt2 (0.6 mL). After 18 hr. additional BF3.OEt2 (0.6 mL) was added. After another 18 hr, the mixture was cooled to 0° C. and carefully quenched with saturated NaHCO3. The resulting mixture was extracted with CH2Cl2 (3×25 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated. The residue was chromatographed on silica gel (50% EtOAc/hexanes) to give the title compound (249 mg, 86% over 3 steps) as a yellow solid: MS (ES) m/e 292 (M+H)+.

Aufarbeitung

  1. waitAfter another 18 hr
  2. customcarefully quenched with saturated NaHCO3
  3. extractionThe resulting mixture was extracted with CH2Cl2 (3×25 mL)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel (50% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-0b032ba556c94df7851ef9bada438bc2
Quelldatensatz
uspto-grants-2005_04
Patentnummer
US06881736B1

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