Tetrabutylammonium Fluoride → (R)-Methyl 5-(3-(3-(hydroxymethyl)-1,1-dioxidoisothiazolidin-2-yl)-propyl)-thiophene-2-carboxylate

HRID 524363Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 524363
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:36][CH2:37][C@H:38]1[CH2:42][CH2:41][S:40](=[O:44])(=[O:43])[N:39]1[CH2:45][CH2:46][CH2:47][C:48]1[S:52][C:51]([C:53]([O:55][CH3:56])=[O:54])=[CH:50][CH:49]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1>C1COCC1.CCOC(C)=O>[OH:36][CH2:37][C@H:38]1[CH2:42][CH2:41][S:40](=[O:43])(=[O:44])[N:39]1[CH2:45][CH2:46][CH2:47][C:48]1[S:52][C:51]([C:53]([O:55][CH3:56])=[O:54])=[CH:50][CH:49]=1

Komponenten

5

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 131735581HCID 131735581, Verbindung

Produkt 1

HCID 118688790(R)-Methyl 5-(3-(3-(hydroxymethyl)-1,1-dioxidoisothiazolidin-2-yl)-propyl)-thiophene-2-carboxylateAusbeute 73,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Tetrabutylammonium fluoride (1.95 mL of a 1.0M solution in THF, 1.95 mmol) was added to a solution of the silyl ether 9 (751 mg, 1.29 mmol) in THF (3.0 mL). After stirring for 16 h the reaction was diluted with EtOAc and washed with water followed by brine. The organic portion was dried (MgSO4), filtered and concentrated in vacuo. Purification of the residue by flash column chromatography (silica gel, 20% EtOAc/hex followed by 40% EtOAc/hex) afforded 317 mg (73%) of alcohol 10.

Aufarbeitung

  1. washwashed with water
  2. dry with materialThe organic portion was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification of the residue by flash column chromatography (silica gel, 20% EtOAc/hex followed by 40% EtOAc/hex)

Quellen und Nachweise

ORD-Eintrag
ord-b03920a0709545f08aea8467b1d94392
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09340534B2

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