1,4-Dioxane → (E)-methyl-2-(2-((4-(2-methoxyethoxy)phenoxy)methyl)-4-chlorophenyl)-3-methoxyacrylate

HRID 1360015노트

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HRID 1360015 반응식
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:23]=[CH:22][C:9]([O:10][CH2:11][C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=2B(O)O)=[CH:8][CH:7]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O1CCOCC1.[CH3:38][O:39][C:40](=[O:46])/[C:41](/I)=[CH:42]\[O:43][CH3:44]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)(=O)C.O>[CH3:38][O:39][C:40](=[O:46])/[C:41](/[C:13]1[CH:14]=[CH:15][C:16]([Cl:18])=[CH:17][C:12]=1[CH2:11][O:10][C:9]1[CH:22]=[CH:23][C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])=[CH:7][CH:8]=1)=[CH:42]/[O:43][CH3:44]

참가 물질

8

반응물 4

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 669702642-((4-(2-Methoxyethoxy)phenoxy)methyl)-4-chlorophenylboronic acidHCID 86624615(E)-methyl-2-iodo-3-methoxy-2-propenoate

생성물 1

HCID 11611173(E)-methyl-2-(2-((4-(2-methoxyethoxy)phenoxy)methyl)-4-chlorophenyl)-3-methoxyacrylate수율 71.3%

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 962Water용매HCID 8857Ethyl Acetate용매

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온도
90 °C

실험 절차

1.1 g (3.3 mmol) of the compound obtained in Step 3, 0.17 g (0.15 mmol) of tetrakis(triphenylphosphine) palladium and 1.96 g (9.0 mmol) of K3PO4 were placed in a flask, and 5 ml of dioxane and 1 ml of water were added thereto. After adding 0.73 g (3.0 mmol) of (E)-methyl-2-iodo-3-methoxy-2-propenoate thereto, the resulting mixture was stirred at 90° C. for 22 hours. The mixture was cooled to room temperature, and 10 ml of ethyl acetate was added thereto. The water layer was separated and extracted twice with 10 ml of ethyl acetate, and the organic layers were combined, washed with 20 ml of water and then with 20 ml of a brine solution, dried over anhydrous MgSO4 and concentrated under a reduced pressure. The resulting residue was subjected to column chromatography using 20% ethyl acetate/hexane as an eluent to obtain 0.87 g (yield 71%) of (E)-methyl-2-(2-((4-(2-methoxyethoxy)phenoxy)methyl)-4-chlorophenyl)-3-methoxyacrylate.

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. customThe water layer was separated
  3. extractionextracted twice with 10 ml of ethyl acetate
  4. washwashed with 20 ml of water
  5. dry with materialwith 20 ml of a brine solution, dried over anhydrous MgSO4
  6. concentrationconcentrated under a reduced pressure

출처 및 근거

ORD 기록
ord-3818a97eb98f46dfbe19fbdbfa4b29db
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07879835B2

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