Methanol → 3-[(4-Methoxy)-tetrahydropyran-4-yl]phenyl-methoxyacetic acid

HRID 890885Notes

Reaction equation

HRID 890885 reaction equation
[CH3:1][O:2][C:3]1([C:9]2[CH:10]=[C:11]([CH2:15][O:16][CH2:17]C(OC)=O)[CH:12]=[CH:13][CH:14]=2)[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.[Li+].[OH-:23].[CH3:24][OH:25]>O>[CH3:1][O:2][C:3]1([C:9]2[CH:10]=[C:11]([CH:15]([O:16][CH3:17])[C:24]([OH:25])=[O:23])[CH:12]=[CH:13][CH:14]=2)[CH2:4][CH2:5][O:6][CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 53803914Methyl 3-[(4-methoxy)-tetrahydropyran-4-yl]phenylmethoxyacetate

Product 1

HCID 696405523-[(4-Methoxy)-tetrahydropyran-4-yl]phenyl-methoxyacetic acidYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of methyl 3-[(4-methoxy)-tetrahydropyran-4-yl]phenylmethoxy-acetate (Step 1) (0.5 g, 1.7 mmol) and LiOH (0.18 g, 4.25 mmol) in 10% water and methanol (5 mL) was stirred for 6 h at room temperature. The solvents were removed at reduced pressure, and the concentrated residue was partitioned between ethyl acetate (100 mL) and 1 N HCl (30 mL). The organic layer was separated and washed with saturated brine (1×100 mL), dried over magnesium sulfate, filtered and concentrated. The concentrated residue was vacuum dried to give 0.46 g (97%) of 3-[(4-methoxy)-tetrahydropyran-4-yl]phenyl-methoxyacetic acid as a yellow solid: HRMS calcd for C15H20O5 280.1311. Found 280.1304.

Workup

  1. customThe solvents were removed at reduced pressure
  2. customthe concentrated residue was partitioned between ethyl acetate (100 mL) and 1 N HCl (30 mL)
  3. customThe organic layer was separated
  4. washwashed with saturated brine (1×100 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customdried

Sources & evidence

ORD record
ord-76785585a78e4b459c40c2f7e0a9f965
Source dataset
uspto-grants-2006_02
Patent number
US06998415B2

Reaction notes

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