Diethylamine → HCID 86746608, 화합물

HRID 1613313노트

반응식

HRID 1613313 반응식
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(NCC)C.Br[C:15]1[CH:16]=[C:17]([CH:24]=[CH:25][CH:26]=1)/[CH:18]=[CH:19]\[C:20]([O:22][CH3:23])=[O:21]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:17]1(/[C:18](/[C:8]#[C:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:19]\[C:20]([O:22][CH3:23])=[O:21])[CH:24]=[CH:25][CH:26]=[CH:15][CH:16]=1

참가 물질

5

반응물 3

HCID 8021DiethylamineHCID 10821PhenylacetyleneHCID 86746609methyl (Z)-3-bromocinnamate

생성물 1

HCID 86746608HCID 86746608, 화합물

시약·촉매·용매 1

HCID 178418476HCID 178418476, 화합물촉매

실험 절차

0.158 g of cuprous iodide and 0.424 g of phenylacetylene were added to 25 ml of a diethylamine solution containing 1.000 g of methyl (Z)-3-bromocinnamate and 0.029 g of bis(triphenylphosphine)dichloropalladium. The mixture was then stirred for 1 hour at room temperature, after which the solvent was distilled off under reduced pressure. Water was added to the residue, and the resulting mixture was extracted twice with benzene. The combined benzene extracts were washed with water, dried over anhydrous sodium sulfate and condensed by evaporation under reduced pressure. The residue was subjected to column chromatography through silica gel (70-230 Tyler mesh, 25 g). Those fractions eluted with a 39:1 by volume mixture of hexane and ethyl acetate were collected to afford 1.043 g of the title compound, melting at 73°-75° C. (after recrystallisation from hexane).

후처리

  1. distillationafter which the solvent was distilled off under reduced pressure
  2. additionWater was added to the residue
  3. extractionthe resulting mixture was extracted twice with benzene
  4. washThe combined benzene extracts were washed with water
  5. dry with materialdried over anhydrous sodium sulfate and condensed by evaporation under reduced pressure
  6. washThose fractions eluted with a 39:1 by volume mixture of hexane and ethyl acetate
  7. customwere collected
  8. customto afford
  9. custom1.043 g of the title compound, melting at 73°-75° C. (after recrystallisation from hexane)

출처 및 근거

ORD 기록
ord-56b3108745cc44c58eb12310a49ea042
출처 데이터셋
uspto-grants-1993_03
특허 번호
US05192766

반응 노트

불러오는 중…