Sulfuric Acid → HCID 22752166, compound

HRID 2163493Notes

Reaction equation

HRID 2163493 reaction equation
C([O:3][C:4](=[CH:9][CH2:10][CH2:11][N:12]1[C:16](=[O:17])[C:15]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]2[C:13]1=[O:22])[C:5]([F:8])([F:7])[F:6])C.S(=O)(=O)(O)O>CCOCC.O>[C:13]1(=[O:22])[N:12]([CH2:11][CH2:10][CH2:9][C:4]([C:5]([F:7])([F:6])[F:8])=[O:3])[C:16](=[O:17])[C:15]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]12

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 54149096HCID 54149096, compound

Product 1

HCID 22752166HCID 22752166, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 20 mmole of N-(3-bromopropyl)phthalimide and 22 mmole of triphenylphosphine in 50 ml of benzene is heated at reflux temperature for 2 days. The solid which separates on cooling is filtered, washed with benzene and dried under reduced pressure to give 3-phthalimidopropyl triphenylphosphonium bromide. To a solution of 100 ml of dry liquid ammonia is added finely divided sodium (0.46 g or 2 × 10-2M) and a catalytic amount of ferric nitrate. When the blue sodium solution turns gray 10 g or 2 × 10-2M of finely powdered 3-phthalimidopropyltriphenylphosphonium bromide is added. After stirring for 15 minutes the ammonia is evaporated under a stream of nitrogen. To the residue is added 100 ml of anhydrous benzene and the solution is boiled for about 10 minutes under nitrogen. The solid residue is filtered pff and to the filtrate, containing salt free 3-phthalimidopropylidene triphenylphosphorane is added 6.6 g of 5 × 10-2M of ethyl trifluoroacetate. The reaction mixture is heated at reflux temperature under nitrogen for 12 hours. Concentration of the solvent leaves a residue which is distilled under high vacuum to afford 2-ethoxy-1,1,1-trifluoro-5-phthalimidopent-2ene. A solution of 3 g of 2-ethoxy-1,1,1-trifluoro-5-phthalimidopent- 2-ene in 50 ml of ether is treated with a solution of 1 M of sulfuric acid in 50 ml of water. The reaction mixture is stirred for one half hour at 25° C. The ether phase is separated, washed with brine, and dried over magnesium sulfate and concenrated to give trifluoromethyl 3-phthalimidopropyl ketone.

Workup

  1. customThe ether phase is separated
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-f2506d7717a34b18a100fe20a19e5d14
Source dataset
uspto-grants-1979_01
Patent number
US04134918

Reaction notes

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