3,4-dihydro-2H-pyran → HCID 69601101, Verbindung

HRID 2215082Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2215082
[OH:1][CH2:2][C@H:3]1[CH2:7][S:6][C:5](=[O:8])[NH:4]1.[O:9]1[CH:14]=[CH:13][CH2:12][CH2:11][CH2:10]1.C(N(CC)CC)C>C(Cl)Cl.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]1[O:1][CH2:2][C@H:3]1[CH2:7][S:6][C:5](=[O:8])[NH:4]1

Komponenten

6

Edukt 3

HCID 80803,4-dihydro-2H-pyranHCID 8471TriethylamineHCID 55288328HCID 55288328, Verbindung

Produkt 1

HCID 69601101HCID 69601101, VerbindungAusbeute 73,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6101p-Toluenesulfonic acidKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 3-3 (3.3 g, 25 mmol) and 20 mg of p-toluenesulfonic acid in CH2Cl2 (100 mL) was added 3,4-dihydro-2H-pyran (2.7 mL, 30 mmol) and the resulting solution was stirred at rt for 30 minutes. Triethylamine (0.1 mL) was added and the solution was concentrated in vacuo. The compound was purified by flash chromatography using 40% EtOAc/hexanes to yield 4 g of 3-4 as a colorless oil. 1H NMR (400 MHz, acetone-d6): δ 7.0 (br s, 1H), 4.6 (s, 1H), 4.0 (m, 1H), 3.8 (m, 2H), 3.6 (m, 3H), 3.3 (dd, 1H), 1.9–1.4 (m, 6H).

Aufarbeitung

  1. concentrationthe solution was concentrated in vacuo
  2. customThe compound was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-cf79a5f571614b9f85bd3f7aed34a75c
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07109223B2

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