Methanol → HCID 68533538, compound

HRID 736703Notes

Reaction equation

HRID 736703 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 (1.7 g, 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-e3d590cd19394831acb99e28ea1048b2
Source dataset
uspto-grants-2009_09
Patent number
US07595406B2

Reaction notes

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