Benzyl mercaptan → 3-Benzylsulfanyl-2-(tetrahydro-pyran-4-yloxymethyl)-propionic acid ethyl ester

HRID 1796140Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1796140
[CH2:1]([O:3][C:4](=[O:15])[C:5]([CH2:7][O:8][CH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)=[CH2:6])[CH3:2].C([O-])(O)=O.[Na+].[CH2:21]([SH:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(O)C.O>[CH2:1]([O:3][C:4](=[O:15])[CH:5]([CH2:7][O:8][CH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)[CH2:6][S:28][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH3:2]

Komponenten

6

Edukt 3

HCID 7509Benzyl mercaptanHCID 516892Sodium BicarbonateHCID 210257162-(Tetrahydro-pyran-4-yloxymethyl)-acrylic acid ethyl ester

Produkt 1

HCID 694384543-Benzylsulfanyl-2-(tetrahydro-pyran-4-yloxymethyl)-propionic acid ethyl esterAusbeute 36,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A suspension of 2-(tetrahydro-pyran-4-yloxymethyl)-acrylic acid ethyl ester (2.2 g, 10.2 mmol) in ethanol (100 ml) was treated with a solution of NaHCO3 (0.86 g, 10.2 mmol) in water ml (10 ml) and benzyl mercaptan (1.21 ml, 10.2 mmol) at room temperature overnight. Ethanol evaporated off under reduced pressure, crude partitioned between ethyl acetate and water, organic layer separated and purified by mplc eluting with 1:9 to 2:8 v/v ethyl acetate-heptane mixture to give the title compound as pale yellow oil (1.27 g). MS: 339 (MH+); LCMS (Protocol B) retention time 4.3 minutes.

Aufarbeitung

  1. customEthanol evaporated off under reduced pressure, crude
  2. custompartitioned between ethyl acetate and water, organic layer
  3. customseparated
  4. custompurified
  5. washby mplc eluting with 1:9 to 2:8 v/v ethyl acetate-heptane mixture

Quellen und Nachweise

ORD-Eintrag
ord-d8812ce882d7483cbcd6dbb7c2a19dc8
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07030116B2

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