HCID 21224204, Verbindung → 4-[4-Phenoxyphenylsulfonylmethyl]-tetrahydropyran-4-carboxylic acid

HRID 1584402

Reaktionsgleichung

Reaktionsgleichung von HRID 1584402
Br[C:2]1[CH:27]=[CH:26][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([S:13]([CH2:16][C:17]3([C:23]([OH:25])=[O:24])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)(=[O:15])=[O:14])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1>C(O)C.O1CCCCC1.[Pd]>[O:6]([C:7]1[CH:8]=[CH:9][C:10]([S:13]([CH2:16][C:17]2([C:23]([OH:25])=[O:24])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)(=[O:15])=[O:14])=[CH:11][CH:12]=1)[C:5]1[CH:26]=[CH:27][CH:2]=[CH:3][CH:4]=1

Komponenten

4

Edukt 1

HCID 21224204HCID 21224204, Verbindung

Produkt 1

HCID 212241664-[4-Phenoxyphenylsulfonylmethyl]-tetrahydropyran-4-carboxylic acidAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 86754372Ethanol tetrahydropyranLösungsmittel

Versuchsvorschrift

A solution of 660 mg (1.45 mmol) of 4-[4-(4-bromophenoxy)phenylsulfonylmethyl]-tetrahydropyran-4 -carboxylic acid in 80% ethanol/tetrahydropyran (40 mL) was hydrogenated at atmospheric pressure for 14 hours using palladium on carbon catalyst, filtered over a celite pad washing with methylene chloride and concentrated in vacuo to afford 4-[4-phenoxyphenylsulfonylmethyl]-tetrahydropyran-4-carboxylic acid as a light orange solid (546 mg, 100%), which was taken directly into the next reaction without further purification: mp 162.5-165.3° C.; IR (KBr) 3431 (br), 1727 cm-1 ; 1HNMR (DMSO-d6) δ 1.67 (ddd, J=14.1, 10.0, 4.0 Hz, 2H), 1.95 (dm, J=14.1 Hz, 2H), 3.47 (mc, 2H), 3.65 (mc, 2H), 3.66 (s, 2H), 7.15 (d, J=8.8 Hz, 2H), 7.27 (t, J=7.4 Hz, 1H), 7.45 (t, J=7.5 Hz, 2H), 7.86 (d, J=7.9 Hz, 2H), 12.74 (s, 1H); 13C NMR (DMSO-d6) δ 32.88 (t), 42.26 (s), 61.75 (t), 63.26 (t), 117.64 (d), 120.11 (d), 125.03 (d), 130.04 (d), 130.39 (s), 134.69 (s), 154.69 (s), 161.53 (s), 174.39 (s); FABHRMS Calcd for C19H21SO6 (M+ +H): 377.1059. Found: 378.1064. Anal. Calcd. for C19H20SO6.0.75H2O: C, 58.52; H, 5.56. Found: C, 58.54; H, 5.19.

Aufarbeitung

  1. filtrationfiltered over a celite pad
  2. washwashing with methylene chloride
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8df1c3b171bc46469c62aad0813b9930
Quelldatensatz
uspto-grants-1999_08
Patentnummer
US05932595

Verknüpfte Notizen

Wird geladen…