Ethyl 2-butynoate → (E)-3-(3-ethoxy-2-fluoro-phenoxy)-but-2-enoic acid ethyl ester

HRID 19111Notes

Reaction equation

HRID 19111 reaction equation
[CH2:1]([O:3][C:4]1[C:5]([F:11])=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)[CH3:2].[CH2:12]([O:14][C:15](=[O:19])[C:16]#[C:17][CH3:18])[CH3:13].N12CCCN=C1CCCCC2>O1CCCC1>[CH2:12]([O:14][C:15](=[O:19])/[CH:16]=[C:17](/[O:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([O:3][CH2:1][CH3:2])[C:5]=1[F:11])\[CH3:18])[CH3:13]

Participants

5

Reactant 3

HCID 78043Ethyl 2-butynoateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 668945083-Ethoxy-2-fluorophenol

Product 1

HCID 66894779(E)-3-(3-ethoxy-2-fluoro-phenoxy)-but-2-enoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred mixture of 3-ethoxy-2-fluoro-phenol (6.00 g, 0.038 mol) and ethyl-2-butynoate (8.60 g, 0.077 mol) in tetrahydrofuran (50 mL) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (5.80 g, 0.038 mol) slowly. After addition was complete the mixture was stirred at reflux for 7 h. Upon completion of the reaction the tetrahydrofuran was removed in vacuo and the residue was diluted in diethyl ether and washed first with 1N aqueous hydrochloric acid, then 10% aqueous sodium hydroxide solution, a saturated sodium chloride solution and dried over magnesium sulfate. The crude product, (E)-3-(3-ethoxy-2-fluoro-phenoxy)-but-2-enoic acid ethyl ester, was obtained as a brown oil (6.00 g, 58%) and used without further purification.

Workup

  1. additionAfter addition
  2. temperatureat reflux for 7 h
  3. customwas removed in vacuo
  4. additionthe residue was diluted in diethyl ether
  5. washwashed first with 1N aqueous hydrochloric acid
  6. dry with material10% aqueous sodium hydroxide solution, a saturated sodium chloride solution and dried over magnesium sulfate

Sources & evidence

ORD record
ord-8176dc49da14495abf623ed52a166703
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Reaction notes

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