Tetrahydrofuran → HCID 131734530, Verbindung

HRID 591530Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 591530
[Cl:1][C:2]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:3]=1[CH2:4][O:5][C:6]1[CH:17]=[CH:16][C:9]2[C@H:10]([CH2:13][CH2:14]O)[CH2:11][O:12][C:8]=2[CH:7]=1.C1COCC1.CS(Cl)(=O)=O.[C:33](=[S:36])([O-:35])[CH3:34].[K+]>CN(C=O)C.CCN(CC)CC>[C:33](=[O:35])([S:36][CH2:14][CH2:13][C@H:10]1[C:9]2[CH:16]=[CH:17][C:6]([O:5][CH2:4][C:3]3[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:2]=3[Cl:1])=[CH:7][C:8]=2[O:12][CH2:11]1)[CH3:34]

Komponenten

7

Edukt 4

HCID 8028TetrahydrofuranHCID 31297Methanesulfonyl chlorideHCID 23670855Potassium ethanethioateHCID 89767792HCID 89767792, Verbindung

Produkt 1

HCID 131734530HCID 131734530, VerbindungAusbeute 71,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a mixture of 2-((3S)-6-((2,4-dichlorobenzyl)oxy)-2,3-dihydro-1-benzofuran-3-yl)ethanol (678 mg) and THF (dry) (20 mL) were added methanesulfonyl chloride (0.310 mL) and Et3N (0.279 mL). The mixture was stirred at room temperature for 30 min. And then DMF (dry) (20.00 mL) and potassium ethanethioate (228 mg) were added to the mixture. The volatiles (THF) were removed by evaporation. The resulting mixture was stirred at 70° C. for 2 h. The mixture was poured into water and extracted with EtOAc. The organic layer was separated, washed successively with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (570 mg).

Aufarbeitung

  1. customThe volatiles (THF) were removed by evaporation
  2. stirringThe resulting mixture was stirred at 70° C. for 2 h
  3. additionThe mixture was poured into water
  4. extractionextracted with EtOAc
  5. customThe organic layer was separated
  6. washwashed successively with water and brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-dc23030cdd664d9092448964fe8fbee6
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238639B2

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