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Tetrabutylammonium Fluoride → BLXA4-me

HRID 1641591
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1641591
[Si]([O:8][C@H:9]([C@H:17]([O:42][Si](C(C)(C)C)(C)C)[CH:18]=[CH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH:26]=[CH:27][C@H:28]([O:34][Si](C(C)(C)C)(C)C)[CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:8][C@H:9]([C@H:17]([OH:42])[CH:18]=[CH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH:26]=[CH:27][C@H:28]([OH:34])[CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 66735491HCID 66735491, Verbindung

Produkt 1

HCID 10222011BLXA4-meAusbeute 96,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

The product of Step 4 was dissolved in THF (1 mL) and cooled to 0° C. Tetra-butyl ammonium fluoride (10 μL, 0.078 mmol) was added and the reaction mixture was warmed to RT and allowed to stir overnight. The reaction mixture was quenched with saturated ammonium chloride, extracted with ether, dried and concentrated. Purification by preparatory TLC (silica plate, 5% MeOH/Ethyl acetate) afforded 6.1 mg (96.8%) of (5S,6R,E)-methyl 5,6-dihydroxy-8-(2((R,E)-3-hydroxyoct-1-enyl)phenyl)oct-7-enoate. 1H NMR (250 Hz, CDCl3): δ 7.38 (m, 2H), 7.22 (m, 2H), 6.86 (t, J=15.4 Hz, 1H), 6.07 (m, 1H), 4.27 (m, 1H), 3.77 (m, 1H), 3.63 (m, 1H), 3.46 (q, J=14 Hz, 6.9 Hz, 1H), 2.35 (t, J=7.5 Hz, 2H), 1.81-1.53 (m, 4H), 1.32-1.16 (m, 7H), 0.915-0.789 (m, 4H). 13C (500 NMR C6D6): δ 173.79, 136.18, 136.12, 135.98, 131.59, 130.34, 136.18, 131.59, 130.34, 128.53, 128.20, 127.81, 127.68, 127.62, 127.47, 127.13, 76.02, 74.36, 72.65, 51.01, 37.92, 33.83, 32.22, 30.15, 25.58, 23.05, 21.57, 14.24.

Aufarbeitung

  1. temperaturethe reaction mixture was warmed to RT
  2. customThe reaction mixture was quenched with saturated ammonium chloride
  3. extractionextracted with ether
  4. customdried
  5. concentrationconcentrated
  6. customPurification by preparatory TLC (silica plate, 5% MeOH/Ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-2f84581c75e84c3d9f3927341333e444
Quelldatensatz
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08115023B2

Notizen zur Reaktion

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