Isopropanol → 1,1-Diisopropoxy-2,2-dimethyl-3-pentanone

HRID 984444

Reaktionsgleichung

Reaktionsgleichung von HRID 984444
[CH:1]([O:10][CH:11]([CH3:13])[CH3:12])([O:6][CH:7]([CH3:9])[CH3:8])OC(C)C.[CH3:14][C:15]1[CH:16]=C[C:18](S(O)(=O)=O)=[CH:19][CH:20]=1.C([OH:28])(C)C>[Cl-].[Na+].O>[CH:11]([O:10][CH:1]([O:6][CH:7]([CH3:8])[CH3:9])[C:15]([CH3:16])([CH3:14])[C:20](=[O:28])[CH2:19][CH3:18])([CH3:12])[CH3:13]

Komponenten

5

Edukt 3

HCID 3776IsopropanolHCID 6101p-Toluenesulfonic acidHCID 78191Propane, 2,2',2''-[methylidynetris(oxy)]tris-

Produkt 1

HCID 113221791,1-Diisopropoxy-2,2-dimethyl-3-pentanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To a solution of keto aldehyde 19 (6.40 g, 50 mmol) in isopropanol (100 mL) was added triisopropyl orthoformate (16.7 mL, 75 mmol) and p-TsOH (951 mg, 5.0 mmol). After the mixture was stirred for 3 h, it was poured into brine (100 mL) and extracted with ether (3×100 mL). The combined organic layers were dried and concentrated in vacuo to give 50 as a pale yellow liquid (10.12 g, 88%: IR (neat) 2976, 2935, 1697, 1460, 1379, 1314, 1174, 1125, 1082, 1028 cm−1; 1H NMR (300 MHz, CDCl3) δ 4.58 (s, 1H), 3.80 (sept, J=6.1 Hz, 2H), 2.51 (q, J=7.2 Hz, 2H), 1.18 (d, J=6.2 Hz, 6H), 1.12 (s, 6H), 1.08 (d, J=6.2 Hz, 6H), 0.95 (t, J=7.2 Hz, 3H); 13C NMR (75 MHz, CDCl3) δ 215.8, 104.0, 70.7, 53.4, 32.8, 23.8, 22.4, 20.3, 8.0; HRMS calcd for C10H19O2 (M-C3H7) 171.1385, found 171.1377.

Aufarbeitung

  1. extractionextracted with ether (3×100 mL)
  2. customThe combined organic layers were dried
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ab62705b7ee941aaad6a8e489f24b046
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06867305B2

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