Tributylphosphine → [4-(3-Bromo-5-cyclopropylmethoxybenzylsulfanyl)-2-methyl-phenoxy]-acetic acid ethyl ester

HRID 549558Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 549558
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13][CH2:14][C:15]2[CH:20]=[C:19]([OH:21])[CH:18]=[C:17]([Br:22])[CH:16]=2)=[CH:9][C:8]=1[CH3:23])[CH3:2].[CH:25]1([CH2:28]O)[CH2:27][CH2:26]1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1COCC1>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13][CH2:14][C:15]2[CH:20]=[C:19]([O:21][CH2:28][CH:25]3[CH2:27][CH2:26]3)[CH:18]=[C:17]([Br:22])[CH:16]=2)=[CH:9][C:8]=1[CH3:23])[CH3:2]

Komponenten

6

Edukt 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 75644CyclopropanemethanolHCID 57791915[4-(3-Bromo-5-hydroxy-benzylsulfanyl)-2-methyl-phenoxy]-acetic Acid Ethyl Ester

Produkt 1

HCID 57791923[4-(3-Bromo-5-cyclopropylmethoxybenzylsulfanyl)-2-methyl-phenoxy]-acetic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

[4-(3-Bromo-5-hydroxy-benzylsulfanyl)-2-methyl-phenoxy]-acetic acid ethyl ester (1.0 g; 2.43 mmol), cyclopropylcarbinol (175 mg; 2.43 mmol) and tributylphosphine (1.07 mL; 4.38 mmol) was dissolved in THF (100 mL) in a dried reaction flask under an atmosphere of nitrogen. 1,1′-(Azodicarbonyl)dipiperidine (1.1 g; 4.38 mmol) dissolved in THF (20 mL) was added to the reaction mixture, which was stirred at room temperature for 16 hours. The reaction mixture was filtered, evaporated to dryness and purified by flash chromatography (ethyl acetate:heptane 1:9→2:3). Yield: 980 mg; 86%; HPLC-MS: m/z: 465.0 (M)+; Rt: 2.74 min.

Aufarbeitung

  1. additionwas added to the reaction mixture, which
  2. filtrationThe reaction mixture was filtered
  3. customevaporated to dryness
  4. custompurified by flash chromatography (ethyl acetate:heptane 1:9→2:3)

Quellen und Nachweise

ORD-Eintrag
ord-82e9692f9b8c4ddb91361efb2cc74840
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07943669B2

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