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

HRID 1516142ノート

反応式

HRID 1516142 の反応式
[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]

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9a7a82dd9a9145ada8a907e3038be509
出典データセット
uspto-grants-2012_07
特許番号
US08227456B2

反応ノート

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