Toluene → (E)-3-biphenyl-4-yl-but-2-en-1-ol

HRID 984303

Reaktionsgleichung

Reaktionsgleichung von HRID 984303
CC(C[AlH]CC(C)C)C.C1(C)C=CC=CC=1.C([O:19][C:20](=O)[CH:21]=[C:22]([C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:26][CH:25]=1)[CH3:23])C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1COCC1.CO>[C:27]1([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:26]=[CH:25][C:24](/[C:22](/[CH3:23])=[CH:21]/[CH2:20][OH:19])=[CH:29][CH:28]=1

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 9357Potassium Sodium TartrateHCID 14487Diisobutylaluminum hydrideHCID 545016723-(4-Biphenylyl)-2-butenoic acid ethyl ester

Produkt 1

HCID 11264581(E)-3-biphenyl-4-yl-but-2-en-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A 1M solution of DIBAL-H in toluene (40 ml, 40 mmol) was added dropwise at −70° C. over 20 min. to a stirred solution of 3-biphenyl-4-yl-but-2-enoic acid ethyl ester (2.66 g, 10.0 mmol) in dry THF (100 ml) and the mixture stirred for 30 min. Methanol (2 ml) was added, followed by saturated aqueous Rochelle's salt (100 ml), and the resulting mixture extracted with ethyl acetate (200 ml), separated and the organic phase washed with brine, dried (Na2SO4), evaporated and dried in vacuo yielding (E)-3-biphenyl-4-yl-but-2-en-1-ol as colorless crystals: 1.94 g (86%)

Aufarbeitung

  1. extractionthe resulting mixture extracted with ethyl acetate (200 ml)
  2. customseparated
  3. washthe organic phase washed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-27295cf882084791ba5c76008a40c68f
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06867218B2

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