Lithium hydroxide, monohydrate → HCID 54303636, compound

HRID 2232475Notes

Reaction equation

HRID 2232475 reaction equation
C([O:3][C:4](=[O:18])[CH2:5][CH2:6][C:7]1([CH3:17])[CH2:12][CH2:11][C:10]2[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=2[O:8]1)C.[O:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1.[OH2:24].[OH2:25].[OH-:26].[Li+]>O>[C:6]([C:5]1[CH:4]=[CH:20][C:21]([O:25][CH2:10][CH2:9][CH2:16][O:26][C:15]2[CH:14]=[CH:13][C:10]3[CH2:11][CH2:12][C:7]([CH3:17])([CH2:6][CH2:5][C:4]([OH:3])=[O:18])[O:8][C:9]=3[CH:16]=2)=[C:22]([CH2:13][CH2:14][CH3:15])[C:23]=1[OH:19])(=[O:24])[CH3:7]

Participants

5

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 21881883Oxolane--water (1/1)HCID 131715791HCID 131715791, compound

Product 1

HCID 54303636HCID 54303636, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 1.55 g of the ester from Example 3 and 35 ml of 1:1 tetrahydrofuran-water was added 2.3 g of lithium hydroxide monohydrate, with stirring. The mixture was stirred at room temperature for 22 hours then diluted with water and extracted 3 times with ether (ether extracts discarded). The aqueous solution was acidified to pH 1 by the addition of saturated aqueous oxalic acid and worked-up with ether in the usual manner. There was obtained 1.4 g (95.8%) of racemic-7-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-3,4-dihydro-2-methyl-2H-1-benzopyran-2-propanoic acid as a viscous yellow oil.

Workup

  1. stirringThe mixture was stirred at room temperature for 22 hours
  2. extractionextracted 3 times with ether (ether extracts discarded)
  3. additionThe aqueous solution was acidified to pH 1 by the addition of saturated aqueous oxalic acid

Sources & evidence

ORD record
ord-080ad1473d484edbae487c2925af3138
Source dataset
uspto-grants-1988_11
Patent number
US04788214

Reaction notes

Loading…