Reaktion #1519116

ord-e6677eb734b14ac8a3076bcfe4b8dc1b

Reaktionsgleichung

CC=CC[C@@H](C(=O)OC)[C@H](O)C(=O)OC
(2S,3R)-3-(2-butenyl)-2-hydroxysuccinic dimethyl ester
→
CCCC[C@@H](C(=O)OC)[C@H](O)C(=O)OC
(2S,3R)-3-(n-butyl)-2-hydroxysuccinic dimethyl ester

Edukte

CC=CC[C@@H](C(=O)OC)[C@H](O)C(=O)OC
(2S,3R)-3-(2-butenyl)-2-hydroxysuccinic dimethyl ester

Reagenzien

[Pd]
Pd/C

Lösungsmittel

CCOC(C)=O
EtOAc

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    FiltrationThe suspension is filtered through Celite
  2. 2
    Waschenwashed with EtOAc (3×)
  3. 3
    Einengenconcentrated in vacuo

Vorschrift

To (2S,3R)-3-(2-butenyl)-2-hydroxysuccinic dimethyl ester B-2 (2.5 g) in EtOAc (50 mL) is added 10% Pd/C (0.25 g) and the reaction stirred under a hydrogen atmosphere for 20 hours. The suspension is filtered through Celite, washed with EtOAc (3×) and then concentrated in vacuo to afford (2S,3R)-3-(n-butyl)-2-hydroxysuccinic dimethyl ester B-3.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07612059B2uspto-grants-2009_11