Reaktion #1622015

Reaktionsgleichung

triethylamine

oxalyl chloride

dimethyl sulfoxide

( 6 )

N-Boc-6-amino-1-hexanol

→

pale yellow oil ( 7 )

Ausbeute 95.6%

N-Boc-6-aminohexanal

Ausbeute 95.6%

Lösungsmittel

methylene choride

methylene chloride

water

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITAfter 10 min. more
2. 2
   SonstigeAfter separation
3. 3
   Extraktionthe aqueous layer was extracted again with methylene chloride
4. 4
   Waschenthe combined organic layers were washed with brine
5. 5
   Trocknendried over sodium sulfate
6. 6
   SonstigeAfter evaporation in vacuo
7. 7
   Sonstigethe residue was chromatographed (Flash, hexane-ethyl acetate, 7:3)

Vorschrift

To a stirred solution of 5.3 mL (7.71 g, 60.7 mmoles) oxalyl chloride in 100 mL methylene choride at -70° C. under argon was added 8.6 mL (10.23 g, 121.5 mmoles) dimethyl sulfoxide in 30 mL methylene chloride. After 2 min. a solution of 12 g (55.2 mmoles) of (6) in 50 mL methylene chloride was added over 5 min. After 20 min. 38.5 mL (27.9 g, 276 mmoles) triethylamine was added. After 10 min. more, the mixture was allowed to warm to 20° C. and 250 mL water was added. After separation, the aqueous layer was extracted again with methylene chloride and the combined organic layers were washed with brine and dried over sodium sulfate. After evaporation in vacuo, the residue was chromatographed (Flash, hexane-ethyl acetate, 7:3) to provide 11.36 g of a pale yellow oil (7).

Quelle