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Toluene → [3-[2-(2,6-Dichlorophenyl)ethyl]-5-(1-methylethyl)-4-isoxazolyl]methanol

HRID 646021
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 646021
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][CH2:10][C:11]1[C:15]([C:16](OC)=[O:17])=[C:14]([CH:20]([CH3:22])[CH3:21])[O:13][N:12]=1.[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1COCC1.CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][CH2:10][C:11]1[C:15]([CH2:16][OH:17])=[C:14]([CH:20]([CH3:22])[CH3:21])[O:13][N:12]=1
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Komponenten

7

Edukt 4

HCID 1140Toluene2×HCID 9357Potassium Sodium TartrateHCID 21225700Diisobutylaluminumhydride2×HCID 59264851Methyl 3-[2-(2,6-dichlorophenyl)ethyl]-5-(1-methylethyl)-4-isoxazolecarboxylate

Produkt 1

HCID 59264863[3-[2-(2,6-Dichlorophenyl)ethyl]-5-(1-methylethyl)-4-isoxazolyl]methanolAusbeute 96,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of methyl 3-[2-(2,6-dichlorophenyl)ethyl]-5-(1-methylethyl)-4-isoxazolecarboxylate (0.900 g, 2.63 mmol) in THF (7.3 mL) was stirred at 0° C. as a 1.5M solution of diisobutylaluminum hydride in toluene (3.7 mL, 5.6 mmol) was added. The solution was allowed to warm to room temperature and stir overnight. Additional diisobutylaluminum hydride in toluene (1.8 mL, 2.7 mmol) was added and the solution was allowed to stir for another 3 hours. Methanol was added followed by a saturated aqueous solution of Rochelle's salt. The solution was stirred for two hours then was partitioned between ethyl acetate and brine. The organic layer was dried with magnesium sulfate, concentrated and purified by chromatography (silica gel, 0-60% ethyl acetate in hexane) to provide the title compound (0.80 g, 51.6% as 0.25EtOAc). 1H NMR (DMSO-d6): δ 7.45 (d, J=8 Hz, 2H), 7.28 (t, J=8 Hz, 1H), 4.89 (t, J=5 Hz, 1H), 4.26 (d, J=5 Hz, 2H), 3.31-3.18 (m, 3H), 2.83-2.79 (m, 2H), 1.21 (d, J=7 Hz, 6H).

Aufarbeitung

  1. additionwas added
  2. stirringto stir for another 3 hours
  3. stirringThe solution was stirred for two hours
  4. customthen was partitioned between ethyl acetate and brine
  5. dry with materialThe organic layer was dried with magnesium sulfate
  6. concentrationconcentrated
  7. custompurified by chromatography (silica gel, 0-60% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-ca5f4c0cdbf84782924e05e38e919cb4
Quelldatensatz
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07705028B2

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