Water → HCID 40148031, compound

HRID 1896544Notes

Reaction equation

HRID 1896544 reaction equation
CON(C)[C:4]([C:6]1[S:7][C:8]2[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][C:9]=2[CH:10]=1)=[O:5].[H-].[H-].[H-].[H-].[Li+].[Al+3].OS([O-])(=O)=O.[K+].O>C1COCC1.CCOC(C)=O>[F:17][C:15]([F:16])([F:18])[C:13]1[CH:12]=[CH:11][C:9]2[CH:10]=[C:6]([CH:4]=[O:5])[S:7][C:8]=2[CH:14]=1

Participants

7

Reactant 4

HCID 962WaterHCID 516920Potassium bisulfateHCID 21226445Aluminium lithium hydrideHCID 58918011HCID 58918011, compound

Product 1

HCID 40148031HCID 40148031, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-15 °C

Procedure

To N-methoxy-N-methyl-6-(trifluoromethyl)-1-benzothiophene-2-carboxamide as a solution in THF (0.2 M) at −15° C. was added a solution of LiAlH4 in THF (0.5 M) dropwise via an addition funnel. After stirring at −15° C. for an additional 30 min, an aqueous 1 N KHSO4 solution was added cautiously via an addition funnel. H2O was added followed by EtOAc. The layers were separated and the aqueous layer was extracted once more with EtOAc. The combined organic layers were washed with 1 N HCl, then washed with brine and dried over magnesium sulfate. The volatiles were removed under reduced pressure to obtain the title compound as an oil that solidified under high vacuum.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted once more with EtOAc
  3. washThe combined organic layers were washed with 1 N HCl
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. customThe volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-af0b41c8e4e140c6a6a1ec0a1767aa9d
Source dataset
uspto-grants-2013_08
Patent number
US08518964B2

Reaction notes

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