1-Iodopropane → HCID 57987551, compound

HRID 1869754Notes

Reaction equation

HRID 1869754 reaction equation
[CH3:1][C:2](C)([O-])[CH3:3].[K+].[F:7][C:8]([F:25])([F:24])[C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][C:10]=1[CH2:19][C:20]([O:22][CH3:23])=[O:21].C(I)CC>C1COCC1>[F:7][C:8]([F:24])([F:25])[C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:17])([F:18])[F:16])=[CH:11][C:10]=1[CH:19]([CH2:1][CH2:2][CH3:3])[C:20]([O:22][CH3:23])=[O:21]

Participants

5

Reactant 3

HCID 336431-IodopropaneHCID 23665647Potassium tert-butoxideHCID 86239125HCID 86239125, compound

Product 1

HCID 57987551HCID 57987551, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Potassium t-butoxide (7.7 ml, 1M in THF, 7.7 mmol) was added to a solution of methyl 2-[2,5-bis(trifluoromethyl)phenyl]acetate (2 g, 7 mmol) in THF at 0° C. The resulting yellow solution was stirred for 40 min. n-Propyl iodide (1.7 g, 10.5 mmol) was added and the mixture stirred for 1 h. The mixture was poured onto HCl (2M) and extracted into EtOAc. The combined organic phases were washed with Na2S2O3 solution, brine, then dried (MgSO4) and concentrated in vacuo to give the product as a yellow oil (2 g, 87%). 1H NMR (400 MHz, CDCl3): δ 0.92 (3H, t, J 7.3), 1.23-1.29 (1H, m), 1.35-1.43 (1H, m), 1.67-1.81 (1H, m), 2.05-2.17 (1H, m), 3.69 (3H, s), 4.10 (1H, t, J 7.5), 7.62 (1H, s, J 8.2), 7.78 (1H, d, J 8.2), 7.90 (1H, s).

Workup

  1. additionwas added
  2. additionThe mixture was poured onto HCl (2M)
  3. extractionextracted into EtOAc
  4. washThe combined organic phases were washed with Na2S2O3 solution, brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-52a5e04094a24b1c98e7a0fc254bb598
Source dataset
uspto-grants-2009_12
Patent number
US07638629B2

Reaction notes

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