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Tetrahydrofuran → {5-[4-(4-Methoxyphenyl)piperazin-1-yl]-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-2-yl}methyl methanesulfonate

HRID 1850519
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1850519
C1COCC1.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][N:17]([C:20]3[C:21]([CH3:34])=[C:22]([CH3:33])[C:23]4[O:27][C:26]([CH2:29][OH:30])([CH3:28])[CH2:25][C:24]=4[C:31]=3[CH3:32])[CH2:16][CH2:15]2)=[CH:10][CH:9]=1.C(N(CC)CC)C.[CH3:42][S:43](Cl)(=[O:45])=[O:44]>O.C(OCC)(=O)C>[CH3:42][S:43]([O:30][CH2:29][C:26]1([CH3:28])[CH2:25][C:24]2[C:31]([CH3:32])=[C:20]([N:17]3[CH2:16][CH2:15][N:14]([C:11]4[CH:10]=[CH:9][C:8]([O:7][CH3:6])=[CH:13][CH:12]=4)[CH2:19][CH2:18]3)[C:21]([CH3:34])=[C:22]([CH3:33])[C:23]=2[O:27]1)(=[O:45])=[O:44]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 46910479{5-[4-(4-Methoxyphenyl)piperazin-1-yl]-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-2-yl}methanol

Produkt 1

HCID 59485125{5-[4-(4-Methoxyphenyl)piperazin-1-yl]-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-2-yl}methyl methanesulfonate
Ausbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of THF (2.0 mL) containing {5-[4-(4-Methoxyphenyl)piperazin-1-yl]-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-2-yl}methanol (200 mg, 0.504 mmol) synthesized in Example 97, triethylamine (102 mg, 1.01 mmol) and methanesulfonyl chloride (87 mg, 0.756 mmol) were serially added under ice-cooling condition, and the mixture was warmed to room temperature and stirred for 15 hours. The reaction solution was diluted with water, and extraction was performed using ethyl acetate. The extract was washed with saturated saline and dried using anhydrous magnesium sulfate. After that, the solvent was removed under reduced pressure. The obtained residue was purified by silica gel chromatography (hexane-ethyl acetate 95:5-75:25) to give 220 mg of the title compound (yield: 92%). An amorphous solid.

Aufarbeitung

  1. additionwere serially added under ice-
  2. temperaturecooling condition
  3. washThe extract was washed with saturated saline
  4. customdried
  5. customAfter that, the solvent was removed under reduced pressure
  6. customThe obtained residue was purified by silica gel chromatography (hexane-ethyl acetate 95:5-75:25)

Quellen und Nachweise

ORD-Eintrag
ord-caf3f91d283a45d8a92eea439c714777
Quelldatensatz
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08957069B2

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