Triethylamine → (1RS, 2SR,6RS,7SR)-4-bromo-5-methoxy-10-oxatricyclo[5.2.1.02,6]dec-4-en-3-one

HRID 407840

Reaktionsgleichung

Reaktionsgleichung von HRID 407840
[Br:1]Br.[CH3:3][O:4][C:5]1[CH:13]2[CH:8]([CH:9]3[O:14][CH:12]2[CH2:11][CH2:10]3)[C:7](=[O:15])[CH:6]=1.C(N(CC)CC)C>ClCCl>[Br:1][C:6]1[C:7](=[O:15])[CH:8]2[CH:13]([C:5]=1[O:4][CH3:3])[CH:12]1[O:14][CH:9]2[CH2:10][CH2:11]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 24408BromineHCID 672834435-Methoxy-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one

Produkt 1

HCID 67283643(1RS, 2SR,6RS,7SR)-4-bromo-5-methoxy-10-oxatricyclo[5.2.1.02,6]dec-4-en-3-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of bromine (0.14 ml, 2.8 mmol) in dichloromethane (5 ml) is added dropwise to a solution of the enol ether (0.48 g, 2.6 mmol) prepared in step 1 in dichloromethane (40 ml) at 0° C. and the reaction mixture is stirred for 1 hour. Triethylamine (0.64 ml, 4.6 mmol) is then added and the reaction mixture is allowed to warm to room temperature and then stirred for 3 hours. The reaction mixture is washed with 2M aqueous hydrochloric acid and brine, dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated under reduced pressure. The residue is purified by column chromatography on silica gel to give (1RS,2SR,6RS,7SR)-4-bromo-5-methoxy-10-oxatricyclo[5.2.1.02,6]dec-4-en-3-one.

Aufarbeitung

  1. stirringstirred for 3 hours
  2. washThe reaction mixture is washed with 2M aqueous hydrochloric acid and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customthe filtrate evaporated under reduced pressure
  6. customThe residue is purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-13fc2705a1474372abe61736e60ceacd
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754242B2

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