Tetrahydrofuran → HCID 462612, Verbindung

HRID 743092Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 743092
C(N(CC)CC)C.[CH:8]1([C:11](Cl)=[O:12])[CH2:10][CH2:9]1.[OH:14][CH2:15][C:16]1[S:17][S:18][C:19]([CH2:22][OH:23])=[CH:20][CH:21]=1.S1C=CC=CS1.[O:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1>CCOCC>[CH:8]1([C:11]([O:14][CH2:15][C:16]2[S:17][S:18][C:19]([CH2:22][O:23][C:34]([CH:33]3[CH2:31][CH2:32]3)=[O:30])=[CH:20][CH:21]=2)=[O:12])[CH2:10][CH2:9]1

Komponenten

7

Edukt 5

HCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 462608[6-(Hydroxymethyl)dithiin-3-yl]methanolHCID 120445651,2-Dithiin

Produkt 1

HCID 462612HCID 462612, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a stirred solution of triethylamine (0.30 mL) in tetrahydrofuran (2.0 mL) at 0° C. was added dropwise cyclopropanecarbonyl chloride (0.10 mL) followed by the addition of 3,6-bis(hydroxymethyl)-1,2-dithiin, Dithiin A (20 mg, 0.113 mmol) in tetrahydrofuran (1.0 mL). After stirring in the dark at room temperature overnight the mixture was diluted with ether (20 mL) and partitioned between 1.0M H3PO4 (80 mL) and diethyl ether (30 mL). The diethyl ether layer was washed with saturated NaHCO3 (100 mL), dried (Na2SO4), and evaporated to give a red oil (31.5 mg): 1H NMR (CDCl3) δ6.38 (s, 2H), 4.71 (s, 4H), 1.67 (m, 2H), 1.04 (m, 4H), 0.92 (m, 4H).

Aufarbeitung

  1. custompartitioned between 1.0M H3PO4 (80 mL) and diethyl ether (30 mL)
  2. washThe diethyl ether layer was washed with saturated NaHCO3 (100 mL)
  3. dry with materialdried (Na2SO4)
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-29a21e21d3714fc7849276b899627a55
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05556875

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