Diketene → HCID 11513976, Verbindung

HRID 1184024Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1184024
[C:1]1([C@H:7]([OH:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:10]=[C:11]1[O:14][C:13](=[O:15])[CH2:12]1>O1CCCC1.CN(C1C=CN=CC=1)C>[O:14]=[C:11]([CH3:10])[CH2:12][C:13]([O:9][C@@H:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:8])=[O:15]

Komponenten

5

Edukt 2

HCID 12661DiketeneHCID 6375161-Phenylethanol, (R)-

Produkt 1

HCID 11513976HCID 11513976, VerbindungAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (R)-1-phenylethanol (6.0 ml, 50 mmol) in dry tetrahydrofuran (75 ml) at room temperature was added 4-(N,N-dimethylamino)pyridine (610 mg, 5.0 mmol) followed by dropwise addition of 4-methyleneoxetan-2-one (3.83 ml, 50 mmol). The reaction was stirred for 12 hours at room temperature, then the solvent removed under reduced pressure. The residue was dissolved in ethyl acetate, poured into a separatory funnel, and washed with 1M aqueous hydrochloric acid, water, saturated aqueous sodium bicarbonate, then brine. The organic phase was separated and the solvent removed under resuced pressure to provide (R)-1-phenylethyl 3-oxobutanoate as a light reddish oil (10.3 g, 100%). 1H NMR (CDCl3, 400 MHz) δ 7.4-7.2 (m, 5H); 5.94 (q, 1H, J=6.6 Hz); 3.45 (s, 2H); 2.22 (s, 3H); 1.56 (d, 3H, J=6.6 Hz).

Aufarbeitung

  1. customthe solvent removed under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. additionpoured into a separatory funnel
  4. washwashed with 1M aqueous hydrochloric acid, water, saturated aqueous sodium bicarbonate
  5. customThe organic phase was separated
  6. customthe solvent removed under resuced pressure

Quellen und Nachweise

ORD-Eintrag
ord-fae3b861a92f40fe8e5bc03001f00913
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08664399B2

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