Diethyl Ether → 3-(4-{[1-(4-Chlorophenyl)-3-(trifluoromethyl)-1H-pyrrol-2-yl]methoxy}-2,3-dimethylphenyl)propan-1-ol

HRID 1404163Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1404163
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[C:9]2[CH2:17][O:18][C:19]2[C:24](F)=[CH:23][C:22]([CH2:26][CH2:27][C:28](OCC)=[O:29])=[CH:21][C:20]=2F)=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:40]([CH:43](C(C([O-])=O)O)O)([O-])=O.[K+].[Na+].C(OCC)C>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]=[CH:11][C:10]([C:13]([F:14])([F:16])[F:15])=[C:9]2[CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:26][CH2:27][CH2:28][OH:29])=[C:21]([CH3:20])[C:40]=2[CH3:43])=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydrideHCID 90405892ethyl 3-(4-((1-(4-chlorophenyl)-3-(trifluoromethyl)-1H-pyrrol-2-yl)methoxy)-3,5-difluorophenyl)propanoate

Produkt 1

HCID 904070273-(4-{[1-(4-Chlorophenyl)-3-(trifluoromethyl)-1H-pyrrol-2-yl]methoxy}-2,3-dimethylphenyl)propan-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of the product prepared in Example 1, Step E (46 mg, 0.10 mmol, 1 eq) in THF (2 mL) at 0° C. under N2 was added LAH (0.20 mL of a 1 M solution in THF, 0.20 mmol, 2 eq). After 1 hr, saturated sodium potassium tartrate (0.5 mL) was added dropwise at first, the solution was warmed to room temperature, diethyl ether was added, washed with brine, dried over MgSO4 and concentrated. The resulting residue was purified by flash chromatography (4 g column) eluting with 10 to 30% EtOAc/heptane to yield 3-(4-{[1-(4-Chlorophenyl)-3-(trifluoromethyl)-1H-pyrrol-2-yl]methoxy}-2,3-dimethylphenyl)propan-1-ol.

Aufarbeitung

  1. washwashed with brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe resulting residue was purified by flash chromatography (4 g column)
  5. washeluting with 10 to 30% EtOAc/heptane

Quellen und Nachweise

ORD-Eintrag
ord-3f629eb3ee2a4e8ea5671c97b6e07148
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08912227B1

Notizen zur Reaktion

Wird geladen…