1,3-Propanediol → 3-[3-(2-Cyanophenylsulfonyloxy)-5-methylphenoxy]propanol

HRID 1977940

Reaktionsgleichung

Reaktionsgleichung von HRID 1977940
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([O:12][C:13]1[CH:14]=[C:15]([OH:20])[CH:16]=[C:17]([CH3:19])[CH:18]=1)(=[O:11])=[O:10])#[N:2].C(P(CCCC)CCCC)CCC.[CH2:34](O)[CH2:35][CH2:36][OH:37].N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1.CCCCCC>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([O:12][C:13]1[CH:14]=[C:15]([CH:16]=[C:17]([CH3:19])[CH:18]=1)[O:20][CH2:34][CH2:35][CH2:36][OH:37])(=[O:11])=[O:10])#[N:2]

Komponenten

7

Edukt 4

HCID 104421,3-PropanediolHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 227226433-(2-Cyanophenylsulfonyloxy)-5-methylphenol

Produkt 1

HCID 186697063-[3-(2-Cyanophenylsulfonyloxy)-5-methylphenoxy]propanolAusbeute 80,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

To a solution of 3-(2-cyanophenylsulfonyloxy)-5-methylphenol (580 mg, 2.0 mmol), as prepared in preceding step, tri-n-butylphosphine (607 mg, 3.0 mmol), and 1,3-propanediol (760 mg, 10 mmol) in tetrahydrofuran (20 mL) was added 1,1′-(azodicarbonyl)dipiperidine (757 mg, 3.0 mmol). The mixture was stirred at room 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 (10% ethyl acetate in dichloromethane) to give the title compound as a colorless oil (560 mg, 80%). 1H-NMR (300 MHz, CDCl3) δ8.11 (m, 1H), 7.94 (m, 1H), 7.77-7.82 (m, 2H), 6.65 (s, 1H, 6.59 (s, 1H), 6.57 (s, 1H), 4.05 (t, J=6.0 Hz, 2H), 3.82 (t, J=6.0 Hz, 2H), 2.26 (s, 3H), 2.00 (m, 2H), 1.76 (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 (10% ethyl acetate in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-5e6a359c43a54bfaa58b4c4f2a74187c
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06235778B1

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