Chloroform → Benzyl (s)-hexahydromandelate

HRID 1860506

Reaktionsgleichung

Reaktionsgleichung von HRID 1860506
[C:1]([OH:11])(=[O:10])[C@H:2]([CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)[OH:3].[OH-].[K+].C(Cl)(Cl)Cl.[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].C(Cl)Cl>[OH:3][C@@H:2]([CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)[C:1]([O:11][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:10]

Komponenten

7

Edukt 4

HCID 6212ChloroformHCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 819912(2s)-Cyclohexyl(hydroxy)acetic acid

Produkt 1

HCID 54322505Benzyl (s)-hexahydromandelate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A flask was charged with (S)-hexahydromandelic acid (0.88 g, 5.56 mmol), Bu4NI (0.4 g, 1.1 mmol) and KOH (11.1 mL, 5.56 mmol, 0.5 M in water). 11 mL of chloroform was added followed by benzyl bromide (0.66 mL, 5.56 mmol). The mixture was refluxed for 5 h then cooled and diluted with 100 ml CH2Cl2. The layers were separated and the organic was dried and concentrated. Flash Chromatography (7/1 hexane/EtOAc) gave the desired product. RF: 0.37 (4:1 v/v hexanes/EtOAc); 1H NMR (300 MHz, CDCl3) δ1.11-1.38 (m, 11H), 2.65 (d, J=6.3 Hz, 1H), 4.06 (dd, J=6.3, 3.5 Hz, 1H), 5.22 (s, 2H), 7.30-7.39 (m, 5H).

Aufarbeitung

  1. temperatureThe mixture was refluxed for 5 h
  2. temperaturethen cooled
  3. customThe layers were separated
  4. customthe organic was dried
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ce15cf35018644f38696ecdf1b75c1e4
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06531484B2

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