Diethylamine → HCID 86746608、化合物

HRID 2380704ノート

反応式

HRID 2380704 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 86746608HCID 86746608、化合物

試薬・触媒・溶媒 1

HCID 178418476HCID 178418476、化合物触媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-cec7875732274252890342e0e5541ca7
出典データセット
uspto-grants-1994_11
特許番号
US05369106

反応ノート

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