1,3-Propanediol → 3-[3-(3-Chlorophenylsulfonyloxy)-5-methylphenoxy]propanol

HRID 442945

Reaktionsgleichung

Reaktionsgleichung von HRID 442945
[Cl:1][C:2]1[CH:3]=[C:4]([S:8]([O:11][C:12]2[CH:13]=[C:14]([OH:19])[CH:15]=[C:16]([CH3:18])[CH:17]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.C(P(CCCC)CCCC)CCC.[CH2:33](O)[CH2:34][CH2:35][OH:36].N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1.CCCCCC>[Cl:1][C:2]1[CH:3]=[C:4]([S:8]([O:11][C:12]2[CH:13]=[C:14]([CH:15]=[C:16]([CH3:18])[CH:17]=2)[O:19][CH2:33][CH2:34][CH2:35][OH:36])(=[O:9])=[O:10])[CH:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 104421,3-PropanediolHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 540176793-(3-Chlorophenylsulfonyloxy)-5-methylphenol

Produkt 1

HCID 537730763-[3-(3-Chlorophenylsulfonyloxy)-5-methylphenoxy]propanolAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

To a solution of 3-(3-chlorophenylsulfonyloxy)-5-methylphenol (450 mg, 1.5 mmol), as prepared in the preceding step, tri-n-butylphosphine (607 mg, 3.0 mmol) and 1,3-propanediol (760 mg, 10 mmol) in anhydrous tetrahydrofuran (20 mL) was added 1,1'-(azodicarbonyl) dipiperidine (757 mg, 3.0 mmol). The mixture was stirred at ambient temperature overnight. Hexane (30 mL) was added to the mixture, and the precipitates were removed by filtration. The filtrate was evaporated in vacuo, and the residue was purified by flash column chromatography (1:1 hexane/ethyl acetate) to give the title compound as a colorless oil (480 mg, 90%). 1H-NMR (300 MHz, CDCl3) δ 7.86 (s, 1H), 7.74 (d, J=7.8 Hz, 1H), 7.64 (d, J=8.1 Hz, 1H), 7.49 (t, J=8.0 Hz, 1H), 6.64 (s, 1H), 6.41 (s, 1H), 6.37 (s, 1H), 4.01 (t, J=6.0 Hz, 2H), 3.82 (t, J=6.0 Hz, 2H), 2.25 (s, 3H), 1.99 (m, 2H), 1.65 (br s, 1H).

Aufarbeitung

  1. customthe precipitates were removed by filtration
  2. customThe filtrate was evaporated in vacuo
  3. customthe residue was purified by flash column chromatography (1:1 hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-84c4ad466d1f49c68ccf93792695d745
Quelldatensatz
uspto-grants-1999_04
Patentnummer
US05891909

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