Ammonium Chloride → Butanoic acid, 2-hydroxy-2-(trifluoromethyl)-, ethyl ester

HRID 1988206Notes

Reaction equation

HRID 1988206 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3](=[O:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH3:12][CH2:13][Mg+].[Br-].[NH4+].[Cl-]>CCOCC>[OH:9][C:3]([C:2]([F:10])([F:11])[F:1])([CH2:12][CH3:13])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2737239Ethyl 3,3,3-trifluoro-2-oxopropanoateHCID 178461630HCID 178461630, compound

Product 1

HCID 57437841Butanoic acid, 2-hydroxy-2-(trifluoromethyl)-, ethyl ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a −78° C. solution of ethyl trifluoropyruvate (129.0 g 758 mmol) in ether was added dropwise within 90 min a solution of EtMgBr 3.0 M in ether (252 mL). The solution was brought over one 1 h to ca. −10° C. and poured over 2 L of saturated NH4Cl. The layers were separated and the aqueous phase extracted with ether (3×500 mL). The organic phases were combined, dried over MgSO4 and the solvent removed. Distillation at 50-65° C. (30 mm Hg) gave the title compound. 1H NMR (400 MHz, acetone-d6): δ 5.4 (s, 1H), 4.35 (q, 2H), 2.07 (m, 1H), 1.83 (m, 1H), 1.3 (t, 3H) and 0.93 (t, 3H).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous phase extracted with ether (3×500 mL)
  3. dry with materialdried over MgSO4
  4. customthe solvent removed
  5. distillationDistillation at 50-65° C. (30 mm Hg)

Sources & evidence

ORD record
ord-6f8b6da1c94d4267ac1cf42488feda7f
Source dataset
uspto-grants-2009_06
Patent number
US07553973B2

Reaction notes

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