Reaktion #456339

Reaktionsgleichung

methyl (S)-(+)-2-[(1,1'-biphenyl)-4-yl]-2-hydroxypropionate

benzyloxyacetyl chloride

→

methyl (S)-(+)-2-[(1,1'-biphenyl)-4-yl]-2-(2-phenylmethoxyacetoyl)oxypropionate

Ausbeute 80.0%

Lösungsmittel

pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas quenched
2. 2
   workup.ADDITIONby pouring into 100 mL of 10% aqueous HCl and 200 mL of ether
3. 3
   SonstigeThe ether fraction was separated
4. 4
   Waschenwashed with 50 mL of 10% aqueous HCl, 50 mL of H2O, 2×50 mL of NaHCO3 solution, 50 mL of H2O, 50 mL of brine
5. 5
   Trocknendried (MgSO4)
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe product was purified over 250 g of SiO2 using initially EtOAc/hexanes (1/9)

Vorschrift

In a dry flask under argon, were mixed 1.3 g (5 mmol) of methyl (S)-(+)-2-[(1,1'-biphenyl)-4-yl]-2-hydroxypropionate, 1.7 mL (10 mmol) of 95% benzyloxyacetyl chloride and 6.1 mL of pyridine. The reaction stirred for 48 hours and was quenched by pouring into 100 mL of 10% aqueous HCl and 200 mL of ether. The ether fraction was separated and washed with 50 mL of 10% aqueous HCl, 50 mL of H2O, 2×50 mL of NaHCO3 solution, 50 mL of H2O, 50 mL of brine, dried (MgSO4) and concentrated. The product was purified over 250 g of SiO2 using initially EtOAc/hexanes (1/9) followed by EtOAc/hexanes (1.5/8.5) as eluant to yield 1.5 g (80% yield) of methyl (S)-(+)-2-[(1,1'-biphenyl)-4-yl]-2-(2-phenylmethoxyacetoyl)oxypropionate.

Quelle