Hydrochloric Acid → methyl (E) 2-[3-(4-acetoxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-prop-1-en-1-yl]-3-methylbenzoate

HRID 2396649ノート

反応式

HRID 2396649 の反応式
[C:1]([O:4][C:5]1[C:13]([CH2:14][CH:15]=[CH2:16])=[C:12]([O:17][CH3:18])[C:11]([CH3:19])=[C:10]2[C:6]=1[C:7](=[O:20])[O:8][CH2:9]2)(=[O:3])[CH3:2].Br[C:22]1[C:31]([CH3:32])=[CH:30][CH:29]=[CH:28][C:23]=1[C:24]([O:26][CH3:27])=[O:25].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl>C(=O)([O-])[O-].[Ag+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C)C=O>[C:1]([O:4][C:5]1[C:13]([CH2:14]/[CH:15]=[CH:16]/[C:22]2[C:31]([CH3:32])=[CH:30][CH:29]=[CH:28][C:23]=2[C:24]([O:26][CH3:27])=[O:25])=[C:12]([O:17][CH3:18])[C:11]([CH3:19])=[C:10]2[C:6]=1[C:7](=[O:20])[O:8][CH2:9]2)(=[O:3])[CH3:2]

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 10823279Methyl 2-Bromo-3-methylbenzoateHCID 190463174-Acetoxy-5-allyl-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran

生成物 1

HCID 86749277methyl (E) 2-[3-(4-acetoxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-prop-1-en-1-yl]-3-methylbenzoate

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 178418647HCID 178418647、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

4-Acetoxy-5-allyl-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran (0.6 g), methyl 2-bromo-3-methylbenzoate (0.92 g), silver carbonate (1.3 g), palladium acetate (0.1 g), triphenylphosphine (0.14 g) and dimethylformamide (70 ml) were heated with stirring at 100° C. for 6 hours, then stirred at ambient temperature for 18 hours. The mixture was poured into ice water and the pH adjusted to 3 by addition of 2N hydrochloric acid. The mixture was extracted with ethyl acetate, and the extract was dried and evaporated. The residue was chromatographed on silica gel, eluting with 7:3 hexane:ethyl acetate, to give methyl (E) 2-[3-(4-acetoxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-prop-1-en-1-yl]-3-methylbenzoate, mp 104°-111° C. (ethyl acetate/hexane).

後処理

  1. stirringstirred at ambient temperature for 18 hours
  2. extractionThe mixture was extracted with ethyl acetate
  3. customthe extract was dried
  4. customevaporated
  5. customThe residue was chromatographed on silica gel
  6. washeluting with 7:3 hexane

出典と根拠

ORDレコード
ord-4cfec3b83ff04aa28a0217528d969d46
出典データセット
uspto-grants-1996_02
特許番号
US05493030

反応ノート

読み込み中…