Lithium Hydroxide → HCID 85615690, compound

HRID 1587575Notes

Reaction equation

HRID 1587575 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)[N:21]=3)=[CH:14][CH:13]=2)[CH:6]=1.[Li+].[OH-].C1(C)C=CC=CC=1.CO>O1CCCC1>[N: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:16]=[CH:17][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:13][CH:14]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 21867641Toluene methanolHCID 85615714HCID 85615714, compound

Product 1

HCID 85615690HCID 85615690, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the ester (5 g, 12.16 mmole) of Step G, in dry tetrahydrofuran (66 mL) is added 1N-LiOH (37 mL, 37 mmole) and the mixture is stirred under nitrogen at room temperature for 2.5 hours (TLC, toluene-MeOH 9:1). The tetrahydrofuran is evaporated and the residue is diluted with water, acidified (to pH 6.5) with 10% acetic acid and extracted with ethyl acetate (3×). The extracts are washed with brine, dried (MgSO4) and evaporated to dryness. The crude product (4.94 g, pale yellow solid) is recrystallized from ethyl acetate to provide 3.65 g (75%) of the pure title compound (white solid, m.p. 146°-147° C.).

Workup

  1. customThe tetrahydrofuran is evaporated
  2. additionthe residue is diluted with water
  3. extractionextracted with ethyl acetate (3×)
  4. washThe extracts are washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated to dryness
  7. customThe crude product (4.94 g, pale yellow solid) is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-c1b01d6824a34f69a7295d37de9ed467
Source dataset
uspto-grants-1993_06
Patent number
US05218124

Reaction notes

Loading…