Methanol → HCID 68533538, compound

HRID 2374687Notes

Reaction equation

HRID 2374687 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13]C)=[O:12])=[C:9]([F:17])[CH:8]=1.[OH-].[Li+].CO>O1CCCC1.O>[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[C:7]1[CH:16]=[CH:15][C:10]([C:11]([OH:13])=[O:12])=[C:9]([F:17])[CH:8]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 68533674HCID 68533674, compound

Product 1

HCID 68533538HCID 68533538, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of EXAMPLE 22A (1. 9 g) in tetrahydrofuran (10 mL) and water (5 mL) was added lithium hydroxide (1 g) in water (5 mL). Methanol was added until homogeneous and the solution stirred at ambient temperature for 4 hours. The mixture was concentrated to 5 mL and the residue acidified to pH 2 with 2 N hydrochloric acid. Ethyl acetate and water were added and the organic phase separated, washed with water, dried over magnesium sulfate, filtered and concentrated to give the title compound (1.7g, 95%). MS (DCI): m/z 227 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated to 5 mL
  2. additionEthyl acetate and water were added
  3. customthe organic phase separated
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4c8c659128db4f218cb92d173a1cde93
Source dataset
uspto-grants-2008_12
Patent number
US07462724B2

Reaction notes

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