Lithium hydroxide, monohydrate → HCID 22731315, compound

HRID 2085602Notes

Reaction equation

HRID 2085602 reaction equation
C([O:3][C:4](=[O:19])[CH2:5][CH2:6][C:7]1[C:15]2[O:14][CH2:13][C:12]([CH3:17])([CH3:16])[C:11]=2[CH:10]=[C:9]([Br:18])[CH:8]=1)C.O.[OH-].[Li+]>CO.O1CCCC1.O>[Br:18][C:9]1[CH:8]=[C:7]([CH2:6][CH2:5][C:4]([OH:19])=[O:3])[C:15]2[O:14][CH2:13][C:12]([CH3:17])([CH3:16])[C:11]=2[CH:10]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 69684695HCID 69684695, compound2×

Product 1

HCID 22731315HCID 22731315, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(5-bromo-3,3-dimethyl-2,3-dihydro-benzofuran-7-yl)-propionic acid ethyl ester (Intermediate 76, 0.875 g, 2.67 mmol) in methanol (15 mL), tetrahydrofuran (15 mL) and water (7 mL) was treated with lithium hydroxide monohydrate (0.68 g, 16 mmol) and the resulting reaction mixture was stirred at room temperature for 1 h. The volatiles were evaporated in vacuo and the residue was diluted with water and washed with diethyl ether. The aqueous phase was neutralized with concentrated hydrochloric acid and the solution was extracted with ether (×3). The combined organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated to afford the title compound as an oily foam (0.64 g, 87%).

Workup

  1. customthe resulting reaction mixture
  2. customThe volatiles were evaporated in vacuo
  3. additionthe residue was diluted with water
  4. washwashed with diethyl ether
  5. extractionthe solution was extracted with ether (×3)
  6. dry with materialThe combined organic phase was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-b49f7a8bcd044cf787a1f9218baed01c
Source dataset
uspto-grants-2004_04
Patent number
US06720423B2

Reaction notes

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