Hydrochloric Acid → Benzyl 1-hydroxycyclopropanecarboxylate

HRID 2104420Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2104420
C(N(CC)CC)C.[CH2:8](Br)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[OH:16][C:17]1([C:20]([OH:22])=[O:21])[CH2:19][CH2:18]1.Cl>O1CCCC1.C(Cl)Cl>[CH2:8]([O:22][C:20]([C:17]1([OH:16])[CH2:19][CH2:18]1)=[O:21])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 8471TriethylamineHCID 27331601-Hydroxy-1-cyclopropanecarboxylic acid

Produkt 1

HCID 22934671Benzyl 1-hydroxycyclopropanecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Triethylamine (1.0 mL) and benzyl bromide (650 μL) were added to a solution of 1-hydroxycyclopropanecarboxylic acid (409 mg) in tetrahydrofuran (3.0 mL), and the mixture was stirred at room temperature for 23 hours. To the reaction mixture were added methylene chloride and 1N aqueous hydrochloric acid to thereby give two layers. The organic layer was washed with saturated aqueous sodium hydrogencarbonate and saturated brine, followed by drying over sodium sulfate, to thereby give a crude product. The crude product was subjected to purification through silica gel column chromatography (hexane:ethyl acetate=4:1), to thereby give the title compound (607 mg).

Aufarbeitung

  1. customto thereby give two layers
  2. washThe organic layer was washed with saturated aqueous sodium hydrogencarbonate and saturated brine
  3. dry with materialby drying over sodium sulfate
  4. customto thereby give a crude product
  5. customThe crude product was subjected to purification through silica gel column chromatography (hexane:ethyl acetate=4:1)

Quellen und Nachweise

ORD-Eintrag
ord-00e63e02203f4244a7671248019f15cf
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07576135B2

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