Hydrochloric Acid → HCID 13170167、化合物

HRID 501814ノート

反応式

HRID 501814 の反応式
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[C:10]([O-])(=O)C.[K+].[C:15]([O:18][CH2:19][CH3:20])(=[O:17])[CH3:16].Cl>CN(C)C=O.C(OCC)(=O)C=C.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[CH:6]([C:5]1[CH:8]=[CH:9][C:2](/[CH:10]=[CH:16]/[C:15]([O:18][CH2:19][CH3:20])=[O:17])=[CH:3][CH:4]=1)=[O:7]

参加物

11

反応物 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 707414-BromobenzaldehydeHCID 517044Potassium Acetate

生成物 1

HCID 13170167HCID 13170167、化合物

試薬・触媒・溶媒 6

HCID 11776Triphenylphosphine触媒HCID 74236Tetrabutylammonium Bromide触媒HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8821Ethyl Acrylate溶媒

反応条件

温度
90 °C

実験手順

5.00 g of 4-bromobenzaldehyde was dissolved in 100 mL of N,N-dimethylformamide, to which 2.9 mL of ethyl acrylate, 0.30 g of palladium(II) acetate, 0.35 g of triphenylphosphine, 13.20 g of potassium acetate, and 8.70 g of tetra-n-butylammonium bromide were added, and this solution was stirred for 2.5 hours at 90° C. The reaction mixture was added to a mixture of ethyl acetate and water, and adjusted to pH 2 with 6M hydrochloric acid, and the organic phase was separated therefrom. After the resultant organic phase was washed with water and a saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate, and the solvent was distilled out under reduced pressure. The resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=2:1] to yield 4.75 g of ethyl (E)-3-(4-formylphenyl)-2-propenoate as yellow solid.

後処理

  1. additionwere added
  2. customthe organic phase was separated
  3. washAfter the resultant organic phase was washed with water
  4. dry with materiala saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled out under reduced pressure
  6. customThe resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=2:1]

出典と根拠

ORDレコード
ord-4e85852a1c8b49a0ae98822f4bc10298
出典データセット
uspto-grants-2010_08
特許番号
US07772285B2

反応ノート

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