Methyl 4-oxobutyrate → Dimethyl 3-formyl-4-hydroxyheptanedioate

HRID 593415

Reaktionsgleichung

Reaktionsgleichung von HRID 593415
[O:1]=[CH:2][CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6]>CN(C=O)C>[CH:2]([CH:3]([CH:2]([OH:1])[CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6])[CH2:4][C:5]([O:7][CH3:8])=[O:6])=[O:1]

Komponenten

3

Edukt 1

HCID 83779Methyl 4-oxobutyrate

Produkt 1

HCID 123250817Dimethyl 3-formyl-4-hydroxyheptanedioate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

(S)-Proline (14.9 mg, 0.13 mmol) was added to a stirred solution of 16 (150 mg, 1.29 mmol) in THF (650 μl). The reaction mixture was stirred at r.t. for 14 h. The reaction mixture was purified directly by column chromatography, eluting with petrol/EtOAc (2:1), to give the aldehydes 17 and SI-3 (as a 3.6:1 mixture of anti:syn diastereoisomers, 91 mg, 61%) as a clear colourless oil. The reaction was also conducted on a 244 mg scale of aldehyde 16 in DMF which gave a 2:1 ratio of anti:syn diastereoisomers (100 mg, 41%).

Aufarbeitung

  1. additionas a 3.6:1 mixture of anti
  2. customgave a 2:1 ratio of anti

Quellen und Nachweise

ORD-Eintrag
ord-e39d86288885447bbe8053d407512a87
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242954B2

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