Lithium Hydroxide → HCID 19849035, compound

HRID 1608280Notes

Reaction equation

HRID 1608280 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][S: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][S: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 19849023HCID 19849023, compound

Product 1

HCID 19849035HCID 19849035, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The ester of Example 15 (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-c54472a1e69c467781f4111f02d80a32
Source dataset
uspto-grants-1989_09
Patent number
US04870098

Reaction notes

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