Tributylphosphine → Ethyl[2-methyl-4-(2-thien-2-ylethoxy)phenoxy]acetate

HRID 9653

反応式

HRID 9653 の反応式
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=1[CH3:14])[CH3:2].[S:16]1[CH:20]=[CH:19][CH:18]=[C:17]1[CH2:21][CH2:22]O.C(P(CCCC)CCCC)CCC>O1CCCC1>[CH2:1]([O:3][C:4](=[O:15])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:22][CH2:21][C:17]2[S:16][CH:20]=[CH:19][CH:18]=2)=[CH:9][C:8]=1[CH3:14])[CH3:2]

参加物

5

反応物 3

HCID 13831TributylphosphineHCID 794002-ThiopheneethanolHCID 21986458Ethyl (4-hydroxy-2-methylphenoxy)acetate2 回

生成物 1

HCID 21986308Ethyl[2-methyl-4-(2-thien-2-ylethoxy)phenoxy]acetate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of ethyl(4-hydroxy-2-methylphenoxy)acetate (intermediate 7, 1.05 g) and 2-(2-thienyl)ethanol (0.64 g) in dry tetrahydrofuran was treated with tri-n-butyl phosphine (1.2 g) and azodicarbonyldimorpholide (1.53 g) and the mixture stirred at ambient temperature for 3 days. The reaction mixture was concentrated and the residue partitioned between ethyl acetate and water. The organic layer was collected, dried over sodium sulfate, concentrated and the residue purified by SPE (Si cartridge) eluting with cyclohexane:ethyl acetate (20:1) to give the title compound as a colourless oil.

後処理

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue partitioned between ethyl acetate and water
  3. customThe organic layer was collected
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customthe residue purified by SPE (Si cartridge)
  7. washeluting with cyclohexane:ethyl acetate (20:1)

出典と根拠

ORDレコード
ord-ae8f35505a5f42f7845c7a23a233be40
出典データセット
uspto-grants-2006_08
特許番号
US07091237B2

関連ノート

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