1,3-Diethyl 2-(4-bromophenyl)-2-methylpropanedioate → 2-(4-Bromophenyl)-2-methylpropane-1,3-diol

HRID 640656Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 640656
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:19])([C:14](OCC)=[O:15])[C:9](OCC)=[O:10])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH3:19])([CH2:14][OH:15])[CH2:9][OH:10])=[CH:6][CH:7]=1

Komponenten

4

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of diethyl 2-(4-bromophenyl)-2-methylmalonate (850 mg, 2.6 mmol) in dry THF (5 mL) at 0° C. was added a 1.0M solution of lithium aluminum hydride in THF (2.6 mL, 2.6 mmol). After stirring for 2 h at 0° C., the mixture was quenched by slow addition of water (5 mL). The mixture was made acidic by addition of 1N HCl and was then extracted with dichloromethane (2×20 mL). The organics were combined, dried over Na2SO4 and evaporated to give 2-(4-bromophenyl)-2-methylpropane-1,3-diol (500 mg, 79%) 1H NMR (400 MHz, DMSO-d6) δ 7.47-7.43 (m, 2H), 7.35-7.32 (m, 2H), 4.59-4.55 (m, 2H), 3.56-3.51 (m, 4H), 1.17 (s, 3H).

Aufarbeitung

  1. customthe mixture was quenched by slow addition of water (5 mL)
  2. additionThe mixture was made acidic by addition of 1N HCl
  3. extractionwas then extracted with dichloromethane (2×20 mL)
  4. dry with materialdried over Na2SO4
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-e9fabb0b936f44b6a0fe2c9c85dfa96f
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691902B2

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