Ethanethioic acid, S-phenyl ester → HCID 86722000, Verbindung

HRID 1398030Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1398030
N1([C:10]([CH:12]2[CH2:17][C:16]([CH3:19])([CH3:18])[O:15][C:14]([CH3:21])([CH3:20])[CH2:13]2)=[O:11])C2C=CC=CC=2N=N1.CCOCC.[Mg+2].[Br-].[Br-].[C:30]([S:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)(=[O:32])[CH3:31].CCN(C(C)C)C(C)C>C(Cl)Cl>[C:34]1([S:33][C:30](=[O:32])[CH2:31][C:10](=[O:11])[CH:12]2[CH2:13][C:14]([CH3:20])([CH3:21])[O:15][C:16]([CH3:18])([CH3:19])[CH2:17]2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Komponenten

6

Edukt 4

HCID 13630Ethanethioic acid, S-phenyl esterHCID 81531DiisopropylethylamineHCID 9903262Magnesium bromide diethyl etherateHCID 86721999Benzotriazol-1-yl-(2,2,6,6-tetramethyl-tetrahydro-pyran-4-yl)-methanone

Produkt 1

HCID 86722000HCID 86722000, VerbindungAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a mixture of benzotriazol-1-yl-(2,2,6,6-tetramethyl-tetrahydro-pyran-4-yl)-methanone (1.70 g, 5.62 mmol), magnesium bromide diethyl etherate (4.14 g, 16.06 mmol), and S-phenyl thioacetate (0.76 mL, 5.35 mmol) in 21 mL of DCM at RT was added dropwise DIEA (3.95 mL, 21.41 mmol). The mixture was stirred overnight and then diluted with 50 mL of DCM and washed with 1N HCl (100 mL) and brine (100 mL). The organic layer was dried over Na2SO4, concentrated, and the residue purified by flash chromatography on silica gel to give 1.2 g (70%) of a colorless oil. Mass spectrum (ESI, m/z): Calculated for C18H24O3S, 321.1 (M+H), found 321.1.

Aufarbeitung

  1. washwashed with 1N HCl (100 mL) and brine (100 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. customthe residue purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-6e58a00dde9744429f0684c3aa76e09d
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901314B2

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