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Triethylamine → 4-Hydroxy-3-(5-hydroxymethyl-2-isopropyl-thiophen-3-ylsulfanyl)-6-isopropyl-6-(2-thiophen-3-yl-ethyl)-5,6-dihydro-pyran-2-one

HRID 23514
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 23514
[OH:1][C:2]1[CH2:7][C:6]([CH:15]([CH3:17])[CH3:16])([CH2:8][CH2:9][C:10]2[CH:14]=[CH:13][S:12][CH:11]=2)[O:5][C:4](=[O:18])[CH:3]=1.C([SiH2][O:24][C:25](C)(C)[C:26]1[S:30][C:29]([CH:31]([CH3:33])[CH3:32])=[C:28]([S:34]S(C2C=CC(C)=CC=2)(=O)=O)[CH:27]=1)(C)(C)C.CCN(CC)CC.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O.C1COCC1.C(#N)C>[OH:1][C:2]1[CH2:7][C:6]([CH:15]([CH3:16])[CH3:17])([CH2:8][CH2:9][C:10]2[CH:14]=[CH:13][S:12][CH:11]=2)[O:5][C:4](=[O:18])[C:3]=1[S:34][C:28]1[CH:27]=[C:26]([CH2:25][OH:24])[S:30][C:29]=1[CH:31]([CH3:33])[CH3:32]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 2724141Tetrabutylammonium FluorideHCID 546770164-Hydroxy-6-isopropyl-6-(2-thiophen-3-yl-ethyl)-5,6-dihydro-pyran-2-oneHCID 131723784HCID 131723784, Verbindung

Produkt 1

HCID 546770324-Hydroxy-3-(5-hydroxymethyl-2-isopropyl-thiophen-3-ylsulfanyl)-6-isopropyl-6-(2-thiophen-3-yl-ethyl)-5,6-dihydro-pyran-2-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The title compound was prepared according to General Method 16b using 4-hydroxy-6-isopropyl-6-(2-thiophen-3-yl-ethyl)-5,6-dihydro-pyran-2-one (Example E-20; 0.200 g, 0.75 mmol), toluene-4-thiosulfonic acid S-[5-(tert-butyl-dimethyl-silanyloxymethyl)-2-isopropyl-thiophen-3-yl]ester (Example BB-9; 0.377 g, 0.83 mmol), NEt3 (0.209 mL, 1.50 mmol), and acetonitrile (1.5 mL). As part of the purification, the silylether was cleaved by dissolving the crude coupled product in THF (50 mL) and then treated with a 1.0 M THF solution of tetrabutylammoniumflouride (1.5 mL, 1.5 mmol). After 30 minutes, the mixture was diluted with H2O and extracted with EtOAc. The organic layers were then combined, dried (MgSO4), and concentrated. The resulting residue was then submitted to column chromatography (eluting with 3% MeOH in CH2Cl2) to provide the title compound, mp 52-54° C.

Aufarbeitung

  1. customThe title compound was prepared
  2. customAs part of the purification
  3. dissolutionby dissolving the crude
  4. extractionextracted with EtOAc
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. washThe resulting residue was then submitted to column chromatography (eluting with 3% MeOH in CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-5ce9fcff9ef043ae914e9fd2b86977c5
Quelldatensatz
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06852711B2

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