Lithium Hydroxide → HCID 85615691, compound

HRID 2380157Notes

Reaction equation

HRID 2380157 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 (3x). 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 (3x)
  4. dry with materialThe extracts are dried (MgSO4)
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-5b3f455b18304d13bd48b06c9bc1c2bb
Source dataset
uspto-grants-1994_11
Patent number
US05364944

Reaction notes

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