Реакция #89788

ord-1c29e8ee799c46e9b7cd1445aa3b90f7

Уравнение реакции

[Cl-]
chloride
COC1C=C(/C=C/CO)C=CC1(O)OC(C)=O
4-acetoxyconiferyl alcohol
COC1C=C(/C=C/C(=O)Cl)C=CC1(O)OC(C)=O
4-acetoxyferuloyl chloride
CCN(CC)CC
Et3N
COC1C=C(/C=C/CO)C=CC1(O)OC(C)=O
4-acetoxyconiferyl alcohol
→
CC(=O)CC(=O)O
diacetate
COc1cc(/C=C/COC(=O)/C=C/c2ccc(O)c(OC)c2)ccc1O
coniferyl ferulate
Выход 94.0%

Реактанты

[Cl-]
chloride
COC1C=C(/C=C/CO)C=CC1(O)OC(C)=O
4-acetoxyconiferyl alcohol
COC1C=C(/C=C/C(=O)Cl)C=CC1(O)OC(C)=O
4-acetoxyferuloyl chloride
CCN(CC)CC
Et3N
COC1C=C(/C=C/CO)C=CC1(O)OC(C)=O
4-acetoxyconiferyl alcohol

Реагенты

CN(C)c1ccncc1
4-(dimethylamino)-pyridine
CN(C)c1ccncc1
DMAP

Растворители

CCOC(C)=O.ClC(Cl)Cl
CHCl3 EtOAc
ClCCl
CH2Cl2
ClCCl
CH2Cl2

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    workup.ADDITIONwere added
  2. 2
    Промывкаwashed successively with aqueous 3% HCl and saturated NH4Cl
  3. 3
    СушкаDrying over MgSO4, evaporation, and purification by flash chromatography [CHCl3/EtOAc (19:1)]

Методика

Coupling of 4-acetoxyferuloyloyl chloride with 4-acetoxyconiferyl alcohol was efficiently carried out using 4-(dimethylamino)-pyridine (DMAP). Thus, 4-acetoxyconiferyl alcohol and 4-acetoxyferuloyl chloride were dissolved in dry CH2Cl2 (120 mL) to which DMAP (0.25 equiv) and Et3N (0.85 equiv) were added. The mixture was stiffed for 2 h, when TLC [CHCl3/EtOAc (5:1)] showed the starting material was converted into a faster moving compound. The solution was diluted with CH2Cl2 and washed successively with aqueous 3% HCl and saturated NH4Cl. Drying over MgSO4, evaporation, and purification by flash chromatography [CHCl3/EtOAc (19:1)] gave the diacetate of coniferyl ferulate (94%) as a pale yellow oil.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US09441235B2uspto-grants-2016_09