Borane → [5'-Isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methanol

HRID 1028495

Reaktionsgleichung

Reaktionsgleichung von HRID 1028495
B.[CH:2]([C:5]1[CH:6]=[CH:7][C:8]([O:24][CH3:25])=[C:9]([C:11]2[C:12]([C:21](O)=[O:22])=[CH:13][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:16]=2)[CH:10]=1)([CH3:4])[CH3:3].C(C1C=CC(OC)=C(C2C(C(N)=O)=CC(C(F)(F)F)=CC=2)C=1)(C)C>C1COCC1>[CH:2]([C:5]1[CH:6]=[CH:7][C:8]([O:24][CH3:25])=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:18])([F:19])[F:20])=[CH:13][C:12]=2[CH2:21][OH:22])[CH:10]=1)([CH3:4])[CH3:3]

Komponenten

5

Edukt 3

HCID 6331BoraneHCID 533636465'-Isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-carboxylic acidHCID 667165875'-Isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-carboxamide

Produkt 1

HCID 53363647[5'-Isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of borane in THF (1 M, 859 μL, 0.859 mmol) was added dropwise to a stirred solution of 5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-carboxylic acid and 5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-carboxamide (3:1, 96.8 mg, 0.286 mmol) in dry THF at room temperature under N2. The reaction was stirred at room temperature for 3 h and carefully quenched with water (10 mL). The mixture was extracted with EtOAc (3×20 mL) and the combined extracts were washed with brine, dried (Na2SO4) and concentrated in vacuo to give the crude product. This was purified by flash chromatography (Si, 125×160 mm, 0-30% EtOAc in hexanes gradient) to afford [5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methanol as a colorless oil. Rf=0.27 (10% EtOAc/hexanes). 1H NMR (CDCl3, 500 MHz) δ 7.89 (br s, 1H), 7.62 (dd, J=8.0, 1.3 Hz, 1H), 7.36 (d, J=8.0 Hz, 1H), 7.29 (dd, J=8.5, 2.3 Hz, 1H), 7.03 (d, J=2.3 Hz, 1H), 6.96 (d, J=8.5, 1H), 4.51 (m, 2H), 3.74 (s, 3H), 2.93 (septet, J=7.0 Hz, 1H), 2.51 (s, 1H), 1.29 (d, J=7.0 Hz, 6H).

Aufarbeitung

  1. customcarefully quenched with water (10 mL)
  2. extractionThe mixture was extracted with EtOAc (3×20 mL)
  3. washthe combined extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customto give the crude product
  7. customThis was purified by flash chromatography (Si, 125×160 mm, 0-30% EtOAc in hexanes gradient)

Quellen und Nachweise

ORD-Eintrag
ord-e201db5433f14aa48d3192ab9897c227
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08735435B2

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