Phenylmalonic acid → 2-Phenyl-1,3-propanediol

HRID 355354

Reaktionsgleichung

Reaktionsgleichung von HRID 355354
[C:1]1([CH:7]([C:11](O)=[O:12])[C:8](O)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC.C1COCC1>[OH:9][CH2:8][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:11][OH:12]

Komponenten

5

Edukt 2

HCID 75791Phenylmalonic acidHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 2541782-Phenyl-1,3-propanediol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To 5.11 g of phenylmalonic acid in 50 mL of ether cooled to 0° C. was added 60 mL of a 1M solution of lithium aluminum hydride in THF. After stirring the mixture at room temperature overnight, the excess lithium aluminum hydride was quenched with ethyl acetate and dilute hydrochloric acid. The 1,3-dihydroxy-2-phenylpropane was isolated by ether extraction, and subsequent purification by flash chromatography gave 1.34 g of product characterized by NMR. This is treated with one equivalent of tosyl chloride in pyridine to afford the monotosylate. The purified monotosylate is heated in acetone with excess sodium iodide (as described in Example 23) to produce the 1-iodo-2-phenyl-3-propanol. Subsequent silylation with trimethylsilyltriflate (as in Example 16) and treatment of the iodosilylether with triphenylphosphine in toluene at 100 ° C. gives the title compound, which is characterized by its NMR and mass spectra.

Aufarbeitung

  1. customthe excess lithium aluminum hydride was quenched with ethyl acetate and dilute hydrochloric acid

Quellen und Nachweise

ORD-Eintrag
ord-d01485bb1dde4ee691f56bb16b924956
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05830875

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