Triphenylphosphine → methyl (RS)-5-[3-(3-methyl-2-thienylmethoxy)phenyl]-4-(2-methylphenyl)-5-oxopentanoate

HRID 322871

Reaktionsgleichung

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.[OH:34][C:35]1[CH:36]=[C:37]([C:41](=[O:56])[CH:42]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=2[CH3:55])[CH2:43][CH2:44][C:45]([O:47][CH3:48])=[O:46])[CH:38]=[CH:39][CH:40]=1.[CH3:57][C:58]1[CH:62]=[CH:61][S:60][C:59]=1[CH2:63]O>O1CCCC1>[CH3:57][C:58]1[CH:62]=[CH:61][S:60][C:59]=1[CH2:63][O:34][C:35]1[CH:36]=[C:37]([C:41](=[O:56])[CH:42]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=2[CH3:55])[CH2:43][CH2:44][C:45]([O:47][CH3:48])=[O:46])[CH:38]=[CH:39][CH:40]=1

Komponenten

Reaktionsbedingungen

Temperatur: 5 °C

Versuchsvorschrift

A solution of triphenylphosphine (1.13 g) in tetrahydrofuran (30 mL) is treated with diisopropyl azodicarboxylate (0.84 mL) at 0-5° C. The suspension is then treated with methyl (RS)-5-(3-hydroxyphenyl)-5-oxo-4-(2-methylphenyl)pentanoate (671 mg) and 3-methyl-2-thienylmethanol (275 mg), and stirred at 5° C. for 15 minutes. The solution is evaporated and the residue is subjected to flash chromatography on silica gel, eluting with a mixture of pentane and ethyl acetate (5:1 v/v), to give methyl (RS)-5-[3-(3-methyl-2-thienylmethoxy)phenyl]-4-(2-methylphenyl)-5-oxopentanoate (350 mg), in the form of an oil. [NMR(CDCl3):- 2.0-2.5(4H,m), 2.25(3H,s),2.5(3H,s), 3.65(3H,s), 4.8(1H,m),5.1 (2H,q),6.85-7.5(10H)].

Aufarbeitung

customThe solution is evaporated
washeluting with a mixture of pentane and ethyl acetate (5:1 v/v)

Quellen und Nachweise

ORD-Eintrag: ord-7d6ff9da47ce431188d4f1f50ec7c1a9
Quelldatensatz: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06211234B1

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