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

HRID 9653

반응식

HRID 9653 반응식
[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]

참가 물질

5

반응물 3

HCID 13831TributylphosphineHCID 794002-ThiopheneethanolHCID 21986458Ethyl (4-hydroxy-2-methylphenoxy)acetate2회

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-ae8f35505a5f42f7845c7a23a233be40
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091237B2

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