Lithium Hydroxide → HCID 85615691, compound

HRID 1460897Notes

Reaction equation

HRID 1460897 reaction equation
C[O:2][C:3](=[O:31])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11](=[O:30])[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]3[CH:29]=[CH:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:21]=3)=[CH:14][CH:13]=2)[CH:6]=1.[Li+].[OH-]>>[CH:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:28]=[CH:29][C:20]=1[CH2:19][O:18][C:15]1[CH:14]=[CH:13][C:12]([C:11]([C:7]2[CH:6]=[C:5]([CH2:4][C:3]([OH:31])=[O:2])[CH:10]=[CH:9][CH:8]=2)=[O:30])=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 3939Lithium HydroxideHCID 86745288HCID 86745288, compound

Product 1

HCID 85615691HCID 85615691, compoundYield 99.3%

Procedure

A solution of the ester (1.29 g, 3.15 mmole) of Step A, is treated dropwise with 1N-LiOH and the mixture is stirred under nitrogen overnight. The solvent is evaporated and the residue is dissolved in water, acidified in the cold with 10% acetic acid (to pH 3) and extracted with ethyl acetate (3×). The extracts are dried (MgSO4) and evaporated to dryness. The residue (1.24 g, quantitative yield) is recrystallized by dissolving it in a relatively large volume of warm ethyl acetate-dichloromethane followed by concentrating to half volume. The precipitate is collected and dried at 45° C. in vacuo (0.610 g, 48.8%), m.p. 150°-152° C.

Workup

  1. customThe solvent is evaporated
  2. dissolutionthe residue is dissolved in water
  3. extractionextracted with ethyl acetate (3×)
  4. dry with materialThe extracts are dried (MgSO4)
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-8d8e5a3412b849d99fe1b0d10c42573f
Source dataset
uspto-grants-1991_12
Patent number
US05071988

Reaction notes

Loading…