Tetrahydrofuran → Ethyl 1-(hydroxymethyl)cyclopropane-1-carboxylate

HRID 1484757

Reaktionsgleichung

Reaktionsgleichung von HRID 1484757
[Li].[CH3:2][C:3]([O-:6])(C)C.C[C:8]([O-:11])(C)C.CC([O-])(C)C.[Al+3].[O:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1>S(=O)(=O)(O)[O-].[Na+]>[OH:18][CH2:22][C:21]1([C:8]([O:6][CH2:3][CH3:2])=[O:11])[CH2:19][CH2:20]1

Komponenten

4

Edukt 2

HCID 8028Tetrahydrofuran2×HCID 6328594Aluminium lithium tri-tert-butoxide hydride

Produkt 1

HCID 12450336Ethyl 1-(hydroxymethyl)cyclopropane-1-carboxylateAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 516919Sodium BisulfateLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A 1M solution of lithium aluminum tri-tert-butoxyhydride in tetrahydrofuran (70.90 mL, 70.90 mmol) was added to a stirred solution of diethyl cyclopropane-1,1′-dicarboxylate (6 g, 32.20 mmol) in tetrahydrofuran (129 mL) at 23° C. The resulting solution was heated to 65° C. and stirred for 24 h. The cooled reaction mixture was diluted with a 10% solution of sodium bisulfate (275 mL) and extracted with ethyl acetate. The combined organic layers were dried (MgSO4), filtered, and concentrated to dryness to give the desired product as a pale yellow oil (4.60, 91%): 1H NMR (300 MHz, CDCl3) δ 4.16 (q, J=7 Hz, 2H), 3.62 (s, 2H), 2.60 (br s, 1H), 1.22-1.30 (m, 5H), 0.87 (dd, J=7, 4 Hz, 2H).

Aufarbeitung

  1. customThe cooled reaction mixture
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-2808f2b3e20444e1a3b7a7e8499cadcb
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09422278B2

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