Pyridine → (E)-3,7-dimethylocta-2,6-dienyl 2-chloroacetate

HRID 922003

반응식

HRID 922003 반응식
[CH3:1][C:2](=[CH:4][CH2:5][CH2:6]/[C:7](=[CH:9]/[CH2:10][OH:11])/[CH3:8])[CH3:3].[C:12]1(=[O:18])OC(=O)C[CH2:13]1.N1C=CC=CC=1.[Cl:25]CCl>CN(C1C=CN=CC=1)C>[Cl:25][CH2:13][C:12]([O:11][CH2:10]/[CH:9]=[C:7](\[CH3:8])/[CH2:6][CH2:5][CH:4]=[C:2]([CH3:1])[CH3:3])=[O:18]

참가 물질

6

반응물 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 7922Succinic anhydrideHCID 637566Geraniol

생성물 1

HCID 5890636(E)-3,7-dimethylocta-2,6-dienyl 2-chloroacetate수율 99%

시약·촉매·용매 1

HCID 142844-(Dimethylamino)pyridine촉매

실험 절차

Geraniol [1] (1.542 g, 10 mmol), succinic anhydride (1.201 g, 12 mmol) and 4-DMAP (10 mg, cat) were suspended in anhydrous dichloromethane (50 ml) under an atmosphere of dry nitrogen. Pyridine (0.791 g, 10 mmol) was added and the reaction mixture was stirred for 24 hrs at room temperature. The reaction mixture was successively washed with 2N HCl and H2O, dried over Na2SO4 and the solvent was evaporated. Remaining volatile material was removed under reduced pressure (0.01 mbar) to yield product [2] as yellow liquid in 99% yield. The product was pure according to 1H NMR and directly subjected to the next step without further purification. 1H-NMR (300 MHz, d6-DMSO) δ(ppm)=12.24 (br s, 1H), 5.29 (t, J=7.0 Hz, 1H), 5.08 (t, 6.7, 1H), 4.55 (d, J=7.1 Hz, 2H), 2.49 (m, 2H), 2.03 (m, 4H), 1.67 (s, 3H), 1.66 (s, 3H), 1.59 (s, 3H). 13C-NMR (75 MHz, d6-DMSO) δ(ppm)=173.3, 172.2, 141.2, 131.1, 123.7, 118.5, 60.7, 38.9, 28.7, 28.6, 25.8, 25.5, 17.5, 16.1.

후처리

  1. washThe reaction mixture was successively washed with 2N HCl and H2O
  2. dry with materialdried over Na2SO4
  3. customthe solvent was evaporated
  4. customwas removed under reduced pressure (0.01 mbar)

출처 및 근거

ORD 기록
ord-674ce5d74402447086dba0a2fdb40a37
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278134B2

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