Diethyl Ether → HCID 57707307, compound

HRID 1191611Notes

Reaction equation

HRID 1191611 reaction equation
[F:1][C:2]([F:7])([F:6])[CH:3]1[O:5][CH2:4]1.C([Li])CCC.CON(C)[C:16](=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(OCC)C>C1COCC1.CCCCCC>[C:17]1([C:16]([C:3]2([C:2]([F:7])([F:6])[F:1])[CH2:4][O:5]2)=[O:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 5207692-(Trifluoromethyl)oxiraneHCID 569575N-Methoxy-N-methylbenzamideHCID 178418339Butyllithium

Product 1

HCID 57707307HCID 57707307, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent2×

Procedure

2.3 ml (26 mmol) 1,1,1-trifluoro-2,3-epoxypropane in 30 ml THF and 8 ml hexane are cooled to −100° C. and 6.3 ml of a 2.5 M n-butyl lithium solution (16 mmol) in hexane are added over 15 minutes while the temperature does not exceed −95° C. 10 Minutes after complete addition 2.0 (12 mmol) g N-methoxy-N-methylbenzamid in 38 ml THF are added over 15 minutes while the temperature does not exceed −95° C. After 5 hours at −100° C. 12 ml diethyl ether are added and the reaction mixture is warmed to room temperature over 14 hours. The reaction is quenched by addition of saturated ammonium chloride solution. The phases were separated and the aqueous layer is extracted twice with ethyl acetate, the combined organic phases washed with brine, dried over sodium sulphate and then evaporated to yield 2.59 g of Phenyl-[2-(trifluoromethyl)oxiranyl]methanone. 1H-NMR (CDCl3); δ=3.07 (dq, 1H), 3.38 (d, 1H), 7.50 (t, 2H), 7.65 (tt, 1H), 8.07 (d, 2H).

Workup

  1. customdoes not exceed −95° C
  2. additionare added over 15 minutes while the temperature
  3. customdoes not exceed −95° C
  4. customThe reaction is quenched by addition of saturated ammonium chloride solution
  5. customThe phases were separated
  6. extractionthe aqueous layer is extracted twice with ethyl acetate
  7. washthe combined organic phases washed with brine
  8. dry with materialdried over sodium sulphate
  9. customevaporated

Sources & evidence

ORD record
ord-f9186245ad524aa4b43d95bc333a09f3
Source dataset
uspto-grants-2014_03
Patent number
US08680117B2

Reaction notes

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