Reaktion #48778

Reaktionsgleichung

DIAD

methyl 3-hydroxy-5-{[phenylmethyl]oxy}benzoate

triphenylphosphine

(R)-(−)-1-methoxy-2-propanol

→

desired compound

Methyl 3-[(1S)-2-methoxy-(1-methylethyl)oxy]-5-{[phenylmethyl]oxy}benzoate

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled in an ice bath
2. 2
   Filtrationfiltered
3. 3
   Waschenwashing the residue with THF (500 mL)
4. 4
   Sonstigeevaporated

Vorschrift

To a solution of methyl 3-hydroxy-5-{[phenylmethyl]oxy}benzoate (77.4 mmol) in THF was added polymer-supported triphenylphosphine (51.7 g of 3 mmol/g loading, 155 mmol) and (R)-(−)-1-methoxy-2-propanol (102 mmol). The stirred solution was blanketed with argon and cooled in an ice bath. A solution of DIAD (116 mmol) was added dropwise by syringe over 10 minutes. The solution was stirred for 20 minutes and filtered, washing the residue with THF (500 mL). The filtrate and washings were combined, and evaporated to give the desired compound which was used without further purification.

Quelle