1-Bromo-5-[2-n-propyl-3-hydroxy-4-acetylphenoxy]-pentane → Diethyl 4-[[[5-(4-acetyl-3-hydroxy-2-propylphenoxy)pentyl]thio]methyl]-1,3-oxathiolane-2,2-dipropanoate

HRID 1383135Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1383135
[SH:1][CH2:2][CH:3]1[CH2:7][O:6][C:5]([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[S:4]1.[CH2:22]([C:25]1[C:37]([OH:38])=[C:36]([C:39](=[O:41])[CH3:40])[CH:35]=[CH:34][C:26]=1[O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]Br)[CH2:23][CH3:24]>C(C(C)=O)C>[C:39]([C:36]1[CH:35]=[CH:34][C:26]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][S:1][CH2:2][CH:3]2[CH2:7][O:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[S:4]2)=[C:25]([CH2:22][CH2:23][CH3:24])[C:37]=1[OH:38])(=[O:41])[CH3:40]

Komponenten

4

Edukt 2

HCID 137632981-Bromo-5-[2-n-propyl-3-hydroxy-4-acetylphenoxy]-pentaneHCID 14405886Diethyl 4-(mercaptomethyl)-1,3-oxathiolane-2,2-dipropanoate

Produkt 1

HCID 14405889Diethyl 4-[[[5-(4-acetyl-3-hydroxy-2-propylphenoxy)pentyl]thio]methyl]-1,3-oxathiolane-2,2-dipropanoateAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

The reaction of the mercaptan from Example 1 (2.0 g, 0.006 mol) and 5-(2-n-propyl-3-hydroxy-4-acetylphenoxy)-1-bromopentane (described in U.S. Pat. No. 4,565,882, Example 1) (2.1 g. 0.06 mol) in methyl ethyl ketone (20 ml) was carried out and worked up in the same manner as described in Example 2. After chromatography on silica gel using 25% ethyl acetate/hexane as eluent, 3.3 g (93%) of the title compound was obtained as an oil.

Quellen und Nachweise

ORD-Eintrag
ord-c4e4942c5ffb4d5ba20cae47951cb3dc
Quelldatensatz
uspto-grants-1989_02
Patentnummer
US04808729

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