Methanol → HCID 87564755, compound

HRID 1945121Notes

Reaction equation

HRID 1945121 reaction equation
C1([C:7]([C:9]2([C:12]([F:15])([F:14])[F:13])C[O:10]2)=[O:8])C=CC=CC=1.[C:16](=O)([O-])[O-].[Cs+].[Cs+].[CH3:22][OH:23]>>[F:13][C:12]([F:15])([F:14])[C:9]([OH:10])([CH2:7][O:8][CH3:16])[CH:22]=[O:23]

Participants

4

Reactant 3

HCID 887MethanolHCID 10796Cesium carbonateHCID 57707307HCID 57707307, compound

Product 1

HCID 87564755HCID 87564755, compound

Procedure

2.59 g (12 mmol) Phenyl-[2-(trifluoromethyl)oxiranyl]methanone are stirred with 8.8 g (27 mmol) Caesium carbonate in 94 ml methanol. The reaction is quenched by addition of water after 3 days. The aqueous layer is extracted with ethyl acetate, the combined organic phases are washed with brine, dried over sodium sulphate and then evaporated to yield 2.87 g 3,3,3-trifluoro-2-hydroxy-2-methoxymethypropan-1-one. 1H-NMR (CDCl3); δ=3.42 (s, 3H), 3.89 (d, 1H), 4.23 (d, 1H), 4.55 (s, 1H), 7.47 (t, 2H), 7.60 (t, 1H), 8.01 (d, 2H).

Workup

  1. customThe reaction is quenched by addition of water after 3 days
  2. extractionThe aqueous layer is extracted with ethyl acetate
  3. washthe combined organic phases are washed with brine
  4. dry with materialdried over sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-62b655921bd047e692d702efc803a225
Source dataset
uspto-grants-2013_03
Patent number
US08394958B2

Reaction notes

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