Lithium Hydroxide → HCID 85615690, compound

HRID 2380155Notes

Reaction equation

HRID 2380155 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 (3x). 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 (3x)
  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-0d881ee76ba74d1faf48af4ff9c4901b
Source dataset
uspto-grants-1994_11
Patent number
US05364944

Reaction notes

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