Tributylphosphine → [4-(3-Bromo-5-cyclopropylmethoxybenzylsulfanyl)-2-methyl-phenoxy]-acetic acid ethyl ester

HRID 1969202ノート

反応式

HRID 1969202 の反応式
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13][CH2:14][C:15]2[CH:20]=[C:19]([OH:21])[CH:18]=[C:17]([Br:22])[CH:16]=2)=[CH:9][C:8]=1[CH3:23])[CH3:2].[CH:25]1([CH2:28]O)[CH2:27][CH2:26]1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1COCC1>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13][CH2:14][C:15]2[CH:20]=[C:19]([O:21][CH2:28][CH:25]3[CH2:27][CH2:26]3)[CH:18]=[C:17]([Br:22])[CH:16]=2)=[CH:9][C:8]=1[CH3:23])[CH3:2]

参加物

6

反応物 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 75644CyclopropanemethanolHCID 57791915[4-(3-Bromo-5-hydroxy-benzylsulfanyl)-2-methyl-phenoxy]-acetic Acid Ethyl Ester

生成物 1

HCID 57791923[4-(3-Bromo-5-cyclopropylmethoxybenzylsulfanyl)-2-methyl-phenoxy]-acetic acid ethyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

[4-(3-Bromo-5-hydroxy-benzylsulfanyl)-2-methyl-phenoxy]-acetic acid ethyl ester (1.0 g; 2.43 mmol), cyclopropylcarbinol (175 mg; 2.43 mmol) and tributylphosphine (1.07 mL; 4.38 mmol) was dissolved in THF (100 mL) in a dried reaction flask under an atmosphere of nitrogen. 1,1′-(Azodicarbonyl)dipiperidine (1.1 g; 4.38 mmol) dissolved in THF (20 mL) was added to the reaction mixture, which was stirred at room temperature for 16 hours. The reaction mixture was filtered, evaporated to dryness and purified by flash chromatography (ethyl acetate:heptane 1:9→2:3). Yield: 980 mg; 86%; HPLC-MS: m/z: 465.0 (M)+; Rt: 2.74 min.

後処理

  1. additionwas added to the reaction mixture, which
  2. filtrationThe reaction mixture was filtered
  3. customevaporated to dryness
  4. custompurified by flash chromatography (ethyl acetate:heptane 1:9→2:3)

出典と根拠

ORDレコード
ord-d92f443ab0ea40358a00cc72e6858e4d
出典データセット
uspto-grants-2013_04
特許番号
US08426473B2

反応ノート

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