Lithium Hydroxide → HCID 67467711, compound

HRID 2171057Notes

Reaction equation

HRID 2171057 reaction equation
[CH3:1][O:2][C:3]1[C:17]([O:18][CH3:19])=[CH:16][CH:15]=[C:14]([C:20]2[CH:21]=[C:22]3[C:26](=[CH:27][CH:28]=2)[C:25](=[O:29])[O:24][CH2:23]3)[C:4]=1[O:5][CH2:6][C:7]([CH3:13])([CH3:12])[C:8]([O:10]C)=[O:9].[OH-].[Li+]>O1CCCC1.O>[CH3:1][O:2][C:3]1[C:17]([O:18][CH3:19])=[CH:16][CH:15]=[C:14]([C:20]2[CH:21]=[C:22]3[C:26](=[CH:27][CH:28]=2)[C:25](=[O:29])[O:24][CH2:23]3)[C:4]=1[O:5][CH2:6][C:7]([CH3:13])([CH3:12])[C:8]([OH:10])=[O:9]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 54578471HCID 54578471, compound

Product 1

HCID 67467711HCID 67467711, compoundYield 63.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of methyl 3-(2,3-dimethoxy-6-(1-oxo-1,3-dihydroisobenzofuran-5-yl)phenoxy)-2,2-dimethylpropanoate (200 mg, 0.49 mmol) in tetrahydrofuran (15 mL) was added lithium hydroxide (102.5 mg, 2.45 mmol) in water (5 mL) and the resultant reaction mixture was stirred at RT for 4 h. The reaction mixture was concentrated under reduced pressure, the residue was acidified using 1N HCl solution to pH 5 and then extracted with ethyl acetate (3×). The combined ethyl acetate layers were washed with brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford the title compound as a solid (120 mg, 63%).

Workup

  1. customthe resultant reaction mixture
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. extractionextracted with ethyl acetate (3×)
  4. washThe combined ethyl acetate layers were washed with brine
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8a2df20ca7a24ed0a6281a44d94828b7
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

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