Iodoethane → HCID 22595510, compound

HRID 865680Notes

Reaction equation

HRID 865680 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])[CH:6]=[CH:7][CH:8]=1.[Li+].[CH3:17][CH:18]([N-]C(C)C)C.C(I)C>C1COCC1>[CH2:17]([CH:10]([CH2:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:14])([F:15])[F:1])[CH:4]=1)[C:11]([OH:13])=[O:12])[CH3:18]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 2724682Lithium diisopropylamideHCID 27776833-(3-Trifluoromethylphenyl)propanoic acid

Product 1

HCID 22595510HCID 22595510, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

1 eq. of 3-(3-trifluoromethylphenyl)propionic acid was converted, in THF and at -78° C., into the dianion using 2 eq. of LDA (stirring for 30 min. at -78° C., then 30 min. at RT). 2 eq. of ethyl iodide were then added at -78° C. and the mixture was subsequently stirred at RT. Acidic working-up using 2N HCl and purification by chromatography yielded 2-ethyl-3-(3-trifluoromethylphenyl)-propionic acid.

Workup

  1. custom30 min.
  2. customat RT
  3. stirringthe mixture was subsequently stirred at RT
  4. custom2N HCl and purification by chromatography

Sources & evidence

ORD record
ord-7007460e7b4b45139c9d4bdbcafe1b49
Source dataset
uspto-grants-1996_10
Patent number
US05567734

Reaction notes

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