Potassium Carbonate → (E)-N-ethyl-N-(6-methoxy-6-methyl-2-hepten-4-ynyl)-5-formyl-2-furylmethylamine

HRID 1756178노트

반응식

HRID 1756178 반응식
O[CH2:2][C:3]1[O:7][C:6]([CH:8]=[O:9])=[CH:5][CH:4]=1.P(Br)(Br)Br.C(=O)([O-])[O-].[K+].[K+].Cl.[CH2:21]([NH:23][CH2:24]/[CH:25]=[CH:26]/[C:27]#[C:28][C:29]([O:32][CH3:33])([CH3:31])[CH3:30])[CH3:22]>C(OCC)C.CN(C)C=O>[CH2:21]([N:23]([CH2:2][C:3]1[O:7][C:6]([CH:8]=[O:9])=[CH:5][CH:4]=1)[CH2:24]/[CH:25]=[CH:26]/[C:27]#[C:28][C:29]([O:32][CH3:33])([CH3:30])[CH3:31])[CH3:22]

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 24614Phosphorus tribromideHCID 2373325-(Hydroxymethyl)furfuralHCID 19917137(E)-N-ethyl-6-methoxy-6-methyl-2-hepten-4-ynylamine hydrochloride

생성물 1

HCID 19917047(E)-N-ethyl-N-(6-methoxy-6-methyl-2-hepten-4-ynyl)-5-formyl-2-furylmethylamine수율 75.2%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매2회HCID 6228Dimethylformamide용매

실험 절차

0.36 g of 5-hydroxymethyl-2-furaldehyde was dissolved in 10 ml of ethyl ether, and under a nitrogen atmosphere, a ethyl ether solution (2 ml) of 0.25 g of phosphorus tribromide was added dropwise at 0° C. After the mixture was stirred at room temperature for 30 minutes, 0.70 g of potassium carbonate and a dimethylformamide solution (15 ml) of 0.62 g of (E)-N-ethyl-6-methoxy-6-methyl-2-hepten-4-ynylamine hydrochloride were added. The mixture was stirred overnight at room temperature, and then worked up in a customary manner. The product was purified by silica gel column chromatography [hexane/ethyl acetate=2/1] to give 0.62 g of (E)-N-ethyl-N-(6-methoxy-6-methyl-2-hepten-4-ynyl)-5-formyl-2-furylmethylamine as a pale yellow oil.

후처리

  1. stirringThe mixture was stirred overnight at room temperature
  2. customThe product was purified by silica gel column chromatography [hexane/ethyl acetate=2/1]

출처 및 근거

ORD 기록
ord-5dfb1540d0c548f88de705e5873b47b8
출처 데이터셋
uspto-grants-1995_08
특허 번호
US05439932

반응 노트

불러오는 중…