Isopropylamine → Methyl 3-hydroxy-3-isopropyl-7-phenylheptanoate

HRID 1107144

Reaktionsgleichung

Reaktionsgleichung von HRID 1107144
[CH:1](N)([CH3:3])[CH3:2].[Li]CCCC.[C:10]([O:16][CH3:17])(=[O:15])[CH2:11]C(C)C.[C:18]1([CH2:24][CH2:25][CH2:26][CH2:27][CH:28]=[O:29])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1>[OH:29][C:28]([CH:1]([CH3:3])[CH3:2])([CH2:27][CH2:26][CH2:25][CH2:24][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:11][C:10]([O:16][CH3:17])=[O:15]

Komponenten

6

Edukt 4

HCID 6363IsopropylamineHCID 11160Methyl isovalerateHCID 561886BenzenepentanalHCID 178418339Butyllithium

Produkt 1

HCID 18790185Methyl 3-hydroxy-3-isopropyl-7-phenylheptanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of 2.4 mL (18.49 mmol, 1.5 eq) of isopropylamine in 50 mL of dry THF at -78° C. under argon is added 9.3 mL (14.8 mmol, 1.2 eq) of 1.6 M BuLi in hexanes solution. This is stirred at -78° C. for 1 hour at which time 1.8 mL (13.56 mmol, 1.1 eq) of methyl isovalerate is added dropwise. This mixture is stirred at -78° C. for 1.5 hours at which time 2 g (12.33 mmol) of 5-phenylpentanal in 10 mL of dry THF is added dropwise. This is stirred at -78° C. for 1 hour, then allowed to warm slowly to 0° C. over 3 hours. The reaction is quenched with saturated NH4Cl solution and then partitioned between ether and saturated NH4Cl solution. The organics are dried (Na2SO4) and concentrated in vacuo. The product is purified by flash silica gel chromatography to afford methyl 3-hydroxy-3-isopropyl-7-phenylheptanoate in the form of a yellow oil. (0.88 g, 26%): 1H-NMR (300 MHz, CDCl3) δ (TMS) 0.95(t, 6H), 1.45(m, 3H), 1.6(m, 3H), 2.08(bs, 1H), 2.15(m, 1H), 2.35(t, 1H), 2.6(t, 2H), 3.68(s, 3H), 3.85(bm, 1H), 7.15(m, 3H), 7.25(m, 2H).

Aufarbeitung

  1. additionis added dropwise
  2. additionis added dropwise
  3. temperatureto warm slowly to 0° C. over 3 hours
  4. customThe reaction is quenched with saturated NH4Cl solution
  5. custompartitioned between ether and saturated NH4Cl solution
  6. dry with materialThe organics are dried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe product is purified by flash silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0ef565c4a07a4253b81827196914cfc3
Quelldatensatz
uspto-grants-2000_05
Patentnummer
US06057369

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