Phenol → (+/-)-(5-Chloro-7-methoxy-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate

HRID 2115984Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2115984
C(O[C:9]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([Cl:17])=[CH:11][C:10]=1[CH2:18][CH:19]([OH:22])[CH2:20][OH:21])C1C=CC=CC=1.[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1.CC1C=CC(S(OCC(O)CC2C=C(Cl)C=C(OC)C=2OCC2C=CC=CC=2)(=O)=O)=CC=1.S(C1C=CC(C)=CC=1)([O-])(=O)=O.CC1C=CC(S(OCC(O)CC2C=C(Cl)C=C(OC)C=2O)(=O)=O)=CC=1.C1(O)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>N1C=CC=CC=1.[Pd]>[CH3:33][C:23]1[CH:28]=[CH:27][C:26]([S:29]([O:21][CH2:20][CH:19]2[CH2:18][C:10]3[CH:11]=[C:12]([Cl:17])[CH:13]=[C:14]([O:15][CH3:16])[C:9]=3[O:22]2)(=[O:31])=[O:30])=[CH:25][CH:24]=1

Komponenten

11

Edukt 8

HCID 996PhenolHCID 73974-Toluenesulfonyl chlorideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 85570p-ToluenesulfonateHCID 68583190(+/-)-3-[2-(Benzyloxy)-5-chloro-3-methoxyphenyl]-1,2-propanediolHCID 86598563(+/-)-3-(5-Chloro-2-hydroxy-3-methoxyphenyl)-2-hydroxypropyl 4-methylbenzenesulfonateHCID 86598564(+/-)-3-[2-(Benzyloxy)-5-chloro-3-methoxyphenyl]-2-hydroxypropyl 4-methylbenzenesulfonate

Produkt 1

HCID 86598566(+/-)-(5-Chloro-7-methoxy-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonateAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 1049PyridineLösungsmittel

Versuchsvorschrift

Treatment of (±)-3-[2-(benzyloxy)-5-chloro-3-methoxyphenyl]-1,2-propanediol (32 g, 0.1 mol) with p-toluenesulfonyl chloride (21 g, 0.11 mol) in pyridine generally according to the procedure described for intermediate 3 provided (±)-3-[2-(benzyloxy)-5-chloro-3-methoxyphenyl]-2-hydroxypropyl 4-methylbenzenesulfonate. Treatment of the tosylate with palladium on carbon (2.32 g, 5 wt. %) generally according to the procedure described for Intermediate 4 afforded (±)-3-(5-chloro-2-hydroxy-3-methoxyphenyl)-2-hydroxypropyl 4-methylbenzenesulfonate. Treatment of the phenol with triphenylphosphine (23.6 g, 0.09 mol) and diisopropyl azodicarboxylate (18.2 g, 0.09 mol) generally according to the procedure described for Intermediate 5 afforded 28 g (76%) of (±)-(5-chloro-7-methoxy-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate as a pale yellow solid. mp 99-102° C.; Anal. calcd. for C17H17ClO5S: C, 55.36; H, 4.65. Found: C, 55.35; H, 4.62.

Quellen und Nachweise

ORD-Eintrag
ord-a1206852beab4ccaa29e1bd184f5c81f
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07435837B2

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