Lithium hydroxide, monohydrate → HCID 54303636, compound

HRID 2231893Notes

Reaction equation

HRID 2231893 reaction equation
C([O:3][C:4](=[O:36])[CH2:5][CH2:6][C:7]1([CH3:35])[CH2:12][CH2:11][C:10]2[CH:13]=[CH:14][C:15]([O:17][CH2:18][CH2:19][CH2:20][O:21][C:22]3[CH:27]=[CH:26][C:25]([C:28](=[O:30])[CH3:29])=[C:24]([OH:31])[C:23]=3[CH2:32][CH2:33][CH3:34])=[CH:16][C:9]=2[O:8]1)C.O1CCCC1.O.O.[OH-].[Li+]>O>[C:28]([C:25]1[CH:26]=[CH:27][C:22]([O:21][CH2:20][CH2:19][CH2:18][O:17][C:15]2[CH:14]=[CH:13][C:10]3[CH2:11][CH2:12][C:7]([CH3:35])([CH2:6][CH2:5][C:4]([OH:36])=[O:3])[O:8][C:9]=3[CH:16]=2)=[C:23]([CH2:32][CH2:33][CH3:34])[C:24]=1[OH:31])(=[O:30])[CH3:29]

Participants

5

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 21881883Oxolane--water (1/1)HCID 54420370HCID 54420370, 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-665823dc096742e3a61853875d22e238
Source dataset
uspto-grants-1988_11
Patent number
US04785017

Reaction notes

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