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

HRID 9653

Reaction equation

HRID 9653 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-ae8f35505a5f42f7845c7a23a233be40
Source dataset
uspto-grants-2006_08
Patent number
US07091237B2

Linked notes

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