Lithium Hydroxide → HCID 19849038, compound

HRID 1608279Notes

Reaction equation

HRID 1608279 reaction equation
[C:1]([C:4]1[CH:30]=[CH:29][C:7]([O:8][CH2:9][CH2:10][CH2:11][S:12][CH2:13][CH:14]2[CH2:18][O:17][C:16]3([CH2:22][CH2:21][CH:20]([CH2:23][C:24]([O:26]CC)=[O:25])[CH2:19]3)[O:15]2)=[C:6]([CH2:31][CH2:32][CH3:33])[C:5]=1[OH:34])(=[O:3])[CH3:2].[Li+].[OH-]>CO>[C:1]([C:4]1[CH:30]=[CH:29][C:7]([O:8][CH2:9][CH2:10][CH2:11][S:12][CH2:13][CH:14]2[CH2:18][O:17][C:16]3([CH2:22][CH2:21][CH:20]([CH2:23][C:24]([OH:26])=[O:25])[CH2:19]3)[O:15]2)=[C:6]([CH2:31][CH2:32][CH3:33])[C:5]=1[OH:34])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 19849014HCID 19849014, compound

Product 1

HCID 19849038HCID 19849038, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The ester of Example 13 (4.87 g, 10 mmol) is stirred overnight at room temperature under N2 with aqueous LiOH solution (2M, 13 ml) in methanol (60 ml). The reaction is concentrated on a rotary evaporator and the residue diluted with water. The resulting solution is washed once with ethyl ether and then acidified to pH 2.5 with 0.5N KHSO4 solution. The aqueous mixture is extracted with ethyl acetate and the organic layer dried over MgSO4.

Workup

  1. concentrationThe reaction is concentrated on a rotary evaporator
  2. additionthe residue diluted with water
  3. washThe resulting solution is washed once with ethyl ether
  4. extractionThe aqueous mixture is extracted with ethyl acetate
  5. dry with materialthe organic layer dried over MgSO4

Sources & evidence

ORD record
ord-213e808b9d11418daea2d71ef1d80139
Source dataset
uspto-grants-1989_09
Patent number
US04870098

Reaction notes

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