반응 #613475

반응 방정식

oxalylchloride

tetradecan-1-ol

triethylamine

DMSO

→

Tetradecanal

용매

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   온도Then the reaction mixture was slowly warmed to 5° C.
2. 2
   기타quenched by addition of water (200 mL)
3. 3
   기타The phases were separated
4. 4
   추출the aqueous phase was extracted with dichloromethane (3×100 mL)
5. 5
   세척The combined organic phases were washed with brine (1×200 mL)
6. 6
   건조dried over MgSO4
7. 7
   기타The solvent was removed under reduced pressure
8. 8
   기타the product was isolated as a white solid, which
9. 9
   기타was used in the next reaction without purification

실험 절차

A solution of oxalylchloride (8.0 mL, 88.0 mmol, 2.2 eq.) in abs. dichloromethane (200 mL) was treated with DMSO (13.6 mL, 192 mmol, 4.8 eq.) at −60° C. After 3 min the reaction mixture was warmed to approx. 15° C. Then a solution of tetradecan-1-ol (8.56 g, 40.0 mmol) in dry dichloromethane (40 mL) and after further 3 min triethylamine (28 mL, 200 mmol, 5.0 eq.) were added. Then the reaction mixture was slowly warmed to 5° C. and quenched by addition of water (200 mL). The phases were separated and the aqueous phase was extracted with dichloromethane (3×100 mL). The combined organic phases were washed with brine (1×200 mL) and dried over MgSO4. The solvent was removed under reduced pressure and the product was isolated as a white solid, which was used in the next reaction without purification. Yield: 10.4 g (100%), purity: 98% (GC).

출처