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

HRID 1855231Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1855231
[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=4.2 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-90a1c93a6b8e4932b8519de00d09528a
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08962856B2

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