3,4-dihydro-2H-pyran → p-Toluenesulfonic acid

HRID 2382924Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2382924
[CH2:1]([O:3][C:4](=O)[CH2:5][CH2:6][CH2:7]O)C.[CH2:10]1[CH2:15]O[CH:13]=[CH:12][CH2:11]1.CC1(C)C2([CH2:25][S:26]([OH:29])(=[O:28])=[O:27])C(CC1CC2)=O>N1C=CC=CC=1>[CH2:5]1[CH2:4][O:3][CH:1]=[CH:7][CH2:6]1.[CH3:1][C:11]1[CH:12]=[CH:13][C:25]([S:26]([OH:29])(=[O:28])=[O:27])=[CH:15][CH:10]=1

Komponenten

6

Edukt 3

HCID 80803,4-dihydro-2H-pyranHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 357772Ethyl 4-hydroxybutanoate

Produkt 2

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyran

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

Scheme 7 depicts the synthesis of intermediate 11e wherein R3 and Y2 are the same and X═Br. Thus, commercially-available 4-hydroxy-butanoic acid ethyl ester 37 is treated with DHP and CSA, or with DHP, TsOH, and pyridine to provide ester 38. Reduction with LiAlD4 affords deuterated alcohol 39, which is treated with either triphenyl phosphine in CCl4 (Sabitha, G et al., Tetrahedron Letters, 2006, (volume date 2007), 48(2): 313-315) or with methanesulfonyl chloride, lithium chloride, and 2,6-lutidine in DMF (Blaszykowski, C et al., Organic Letters, 2004, 6(21): 3771-3774) to afford chloride 40. Following the same methods as in Scheme 6, chloride 40 may be converted to 11e.

Quellen und Nachweise

ORD-Eintrag
ord-0fd0c98608a64c5f962e12c9cc043be3
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263601B2

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