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 2396649노트

반응식

HRID 2396649 반응식
[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]

참가 물질

8

반응물 4

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

생성물 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

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 178418647HCID 178418647, 화합물촉매HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4cfec3b83ff04aa28a0217528d969d46
출처 데이터셋
uspto-grants-1996_02
특허 번호
US05493030

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