Lithium Hydroxide → HCID 71279403, compound

HRID 2171205Notes

Reaction equation

HRID 2171205 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[C:18]([O:19][CH3:20])=[CH:17][CH:16]=[C:15]([C:21]3[CH:22]=[C:23]4[C:27](=[CH:28][CH:29]=3)[C:26](=[O:30])[O:25][CH2:24]4)[C:7]=2[O:8][CH2:9][C:10]([O:12]CC)=[O:11])[CH2:3][CH2:2]1.[OH-].[Li+]>O1CCCC1.O>[CH:1]1([CH2:4][O:5][C:6]2[C:18]([O:19][CH3:20])=[CH:17][CH:16]=[C:15]([C:21]3[CH:22]=[C:23]4[C:27](=[CH:28][CH:29]=3)[C:26](=[O:30])[O:25][CH2:24]4)[C:7]=2[O:8][CH2:9][C:10]([OH:12])=[O:11])[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 71279395HCID 71279395, compound

Product 1

HCID 71279403HCID 71279403, compoundYield 71.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of ethyl 2-(2-(cyclopropylmethoxy)-3-methoxy-6-(1-oxo-1,3-dihydroisobenzofuran-5-yl)phenoxy)acetate (300 mg, 0.726 mmol) in tetrahydrofuran (15 mL) was added lithium hydroxide (152 mg, 3.631 mmol) in water (5 mL) and the reaction mixture was stirred at RT for 4 h. The reaction mixture was diluted with water and extracted with ethyl acetate (3×). The combined ethyl acetate layers were washed with water, dried over sodium sulphate and concentrated under reduced pressure to afford the 2-(2-(Cyclopropylmethoxy)-3-methoxy-6-(1-oxo-1,3-dihydroisobenzofuran-5-yl)phenoxy)acetic acid as a solid (200 mg, 71.5%).

Workup

  1. extractionextracted with ethyl acetate (3×)
  2. washThe combined ethyl acetate layers were washed with water
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d39a0814666444db834157cc2f169869
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

Loading…