Triphenylphosphine → Methyl (R)-4-Chloro-3-hydroxybutyrate

HRID 529998Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 529998
[OH:1][C@@H:2]([CH2:8]O)[CH2:3][C:4]([O:6][CH3:7])=[O:5].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C(=O)N([Cl:36])C(=O)C1>C(Cl)Cl>[Cl:36][CH2:8][C@H:2]([OH:1])[CH2:3][C:4]([O:6][CH3:7])=[O:5]

Komponenten

5

Edukt 3

HCID 11776TriphenylphosphineHCID 31398ChlorosuccinimideHCID 9877378methyl (3R)-3,4-dihydroxybutanoate

Produkt 1

HCID 10920707Methyl (R)-4-Chloro-3-hydroxybutyrateAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

To a solution of (R)-methyl 3,4-dihydroxybutanoate (125.1 g, 0.93 mol) in CH2Cl2 (1.8 L) was added PPh3 (244.5 g, 0.93 mol) and slowly added NCS (124.2 g, 0.93 mol) under ice water cooling. The mixture was stirred at 5° C. for 20 min and then stirred for 18 h at room temperature. After evaporating the solvent, the residue was purified by column chromatography (P.E\E.A 20:1-5:1, gradient) to give (R)methyl 4-chloro-3-hydroxybutanoate (33 g, 26% over 3 steps). 1H NMR (300 MHz, CDCl3)δ 4.18-4.25 (m, 1H), 3.68 (s, 3H), 3.55-3.60 (m, 2H), 3.32-3.33 (d, J=42 Hz, 1H), 2.52-2.68 (m, 2H).

Aufarbeitung

  1. stirringstirred for 18 h at room temperature
  2. customAfter evaporating the solvent
  3. customthe residue was purified by column chromatography (P.E\E.A 20:1-5:1, gradient)

Quellen und Nachweise

ORD-Eintrag
ord-e6ab91237c684a90b70759f606c89db9
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09351962B2

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