5-[(tert-Butyldiphenylsilyloxy)methyl]-5-[(tetradecanoyloxy)methyl]-tetrahydro-2-furanone → 5-[(Tetradecanoyloxy)methyl]-5-hydroxymethyl-tetrahydro-2-furanone

HRID 363497Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 363497
[Si]([O:18][CH2:19][C:20]1([CH2:26][O:27][C:28](=[O:42])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[O:24][C:23](=[O:25])[CH2:22][CH2:21]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1>C1COCC1>[C:28]([O:27][CH2:26][C:20]1([CH2:19][OH:18])[O:24][C:23](=[O:25])[CH2:22][CH2:21]1)(=[O:42])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]

Komponenten

3

Edukt 1

HCID 108412125-[(tert-Butyldiphenylsilyloxy)methyl]-5-[(tetradecanoyloxy)methyl]-tetrahydro-2-furanone

Produkt 1

HCID 107844975-[(Tetradecanoyloxy)methyl]-5-hydroxymethyl-tetrahydro-2-furanoneAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 3d (0.118 g, 0.2 mmol) in THF (3 mL) at room temperature was stirred with a solution of n-tetrabutylammonium fluoride in THF (1M, 0.3 mL) for 40 min. The solution was evaporated under vacuum, dissolved in EtOAc (20 mL), dried (Na2SO4) and concentrated. The residue obtained was purified by flash column chromatography over silica gel using hexane:EtOAc (7:3) as eluant to give 3e (0.051 g, 72%) as a white solid; mp 65°-66° C. (EtOAc/hexane); IR (KBr) 3448.1, 1763.2, 1728.1 cm-1 ; 1H NMR (CDCl3) δ 0.88 (distorted t, 3 H, CH3), 1.30 (m, 20 H, CH3 (CH2)10CH2CH2CO); 1.60 (m, 2 H, CH3 (CH2)10CH2CH2CO), 2.00-2.12 (m, 2 H, H-4a), 2.20-2.30 (m, 2 H, H-4b), 2.33 (t, J=7.6 Hz, 2 H, CH3 (CH2)10CH2CH2CO), 2.45 (t, J=6.4 Hz, 1 H, OH), 2.65 (m, 2 H, H-3), 3.60 (dd, J=12.1, 5.9 Hz, 1 H, CHHOH), 3.75 (dd, J=12.1, 6.1 Hz, CHHOH), 4.10 (d, J=12.0 Hz, 1 H, CHHOCO), 4.30 (d, J=12.0 Hz, 1 H, CHHOCO); 13C NMR δ 14.09, 22.65, 24.81, 25.47, 28.79, 29.07, 29.19, 29.32, 29.41, 29.56, 29.60, 31.89, 34.03, 64.82, 65.45, 86.02, 173.48, 176.47; FAB MS (m/z, relative intensity) 357 (MH+, 100), 211 (C13H27CO+, 35). Anal. Calcd for C20H36O5 : C,67.37; H,10.18. Found: C,67.30; H,10.17.

Aufarbeitung

  1. customThe solution was evaporated under vacuum
  2. dissolutiondissolved in EtOAc (20 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue obtained
  6. customwas purified by flash column chromatography over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-ab954ab3b50a452db972e67f33be0aa2
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05874464

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