Chloride → Coniferyl ferulate

HRID 61510

反応式

HRID 61510 の反応式
[Cl-].C([O:5][C:6]1([OH:18])[CH:15]=[CH:14][C:9](/[CH:10]=[CH:11]/[CH2:12][OH:13])=[CH:8][CH:7]1[O:16][CH3:17])(=O)C.C([O:22][C:23]1(O)[CH:33]=[CH:32][C:26](/[CH:27]=[CH:28]/[C:29](Cl)=[O:30])=[CH:25][CH:24]1[O:34][CH3:35])(=[O:21])C.CCN(CC)CC>CN(C)C1C=CN=CC=1.C(Cl)Cl.C(Cl)(Cl)Cl.CCOC(C)=O>[CH3:9][C:8]([CH2:7][C:6]([OH:18])=[O:5])=[O:21].[C:29]([O:13][CH2:12]/[CH:11]=[CH:10]/[C:9]1[CH:14]=[CH:15][C:6]([OH:18])=[C:7]([O:16][CH3:17])[CH:8]=1)(=[O:30])/[CH:28]=[CH:27]/[C:26]1[CH:32]=[CH:33][C:23]([OH:22])=[C:24]([O:34][CH3:35])[CH:25]=1

参加物

9

反応物 4

HCID 312ChlorideHCID 8471TriethylamineHCID 1317371784-Acetoxyconiferyl alcohol2 回HCID 1317371794-Acetoxyferuloyl chloride

生成物 2

HCID 96Acetoacetic AcidHCID 6441913Coniferyl ferulate収率 94%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒2 回HCID 6344Dichloromethane溶媒2 回HCID 21584013Chloroform ethylacetate溶媒

実験手順

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.

後処理

  1. additionwere added
  2. washwashed successively with aqueous 3% HCl and saturated NH4Cl
  3. dry with materialDrying over MgSO4, evaporation, and purification by flash chromatography [CHCl3/EtOAc (19:1)]

出典と根拠

ORDレコード
ord-1c29e8ee799c46e9b7cd1445aa3b90f7
出典データセット
uspto-grants-2016_09
特許番号
US09441235B2

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