Trifluoroacetic acid → 4-[4-(2-Pyrrolidin-1-yl-ethoxy)-benzyl]-phenol

HRID 1180040

Reaktionsgleichung

Reaktionsgleichung von HRID 1180040
Br[C:2]1[CH:15]=[CH:14][C:5]([O:6][CH2:7][CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1.C[Si](C)(C)[O:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>C1COCC1.C(Cl)Cl>[N:9]1([CH2:8][CH2:7][O:6][C:5]2[CH:14]=[CH:15][C:2]([CH2:23][C:22]3[CH:25]=[CH:26][C:19]([OH:18])=[CH:20][CH:21]=3)=[CH:3][CH:4]=2)[CH2:13][CH2:12][CH2:11][CH2:10]1

Komponenten

7

Edukt 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 70536p-((Trimethylsilyl)oxy)benzaldehydeHCID 70657N-(2-(p-bromophenoxy)ethyl)pyrrolidine

Produkt 1

HCID 220479654-[4-(2-Pyrrolidin-1-yl-ethoxy)-benzyl]-phenolAusbeute 94,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 1-[2-(4-bromo-phenoxy)-ethyl]-pyrrolidine (2.89 g, 10.7 mmol) in THF (30 mL) was added dropwise 1.6 M solution in hexanes n-BuLi (7 mL, 10.2 mmol) over a 5-min period at −78° C. The mixture was stirred at −78° C. for 15 min before 4-trimethylsilyloxybenzaldehyde (2.08 g, 10.7 mmol) was added. The mixture was allowed to warm to rt during 20 min and quenched with water. Extraction with CH2Cl2, drying (MgSO4), filtration and evaporation provided the crude diarylmethanol which was dissolved in CH2Cl2 (30 mL) and stirred with triethylsilane (4 mL) and TFA (5 mL) for 16 h at rt. Evaporation gave 3.0 g (84%) 4-[4-(2-pyrrolidin-1-yl-ethoxy)-benzyl]-phenol. This was carbamoylated using general procedure 1 (CH2Cl2 was used as solvent) to give the title product after purification by preparative HPLC (Gilson) (35%, oil).

Aufarbeitung

  1. additionwas added
  2. customquenched with water
  3. extractionExtraction with CH2Cl2
  4. customdrying
  5. filtration(MgSO4), filtration and evaporation
  6. customprovided the crude diarylmethanol which
  7. customEvaporation

Quellen und Nachweise

ORD-Eintrag
ord-47bbc5c9258c42a59a954da5675c2c30
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07279470B2

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