Lithium hydroxide, monohydrate → HCID 57467446, compound

HRID 1890788Notes

Reaction equation

HRID 1890788 reaction equation
O.[OH-].[Li+].[Cl:4][C:5]1[CH:6]=[C:7]([CH:18]=[CH:19][CH:20]=1)[O:8][C:9]1([C:13]([O:15]CC)=[O:14])[CH2:12][CH2:11][CH2:10]1>O1CCCC1.O>[Cl:4][C:5]1[CH:6]=[C:7]([CH:18]=[CH:19][CH:20]=1)[O:8][C:9]1([C:13]([OH:15])=[O:14])[CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 57467445HCID 57467445, compound

Product 1

HCID 57467446HCID 57467446, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

Lithium hydroxide monohydrate (1.7 g, 40.3 mmol) was added to a suspension of Example 15A (4.7 g, 13.4 mmol) in tetrahydrofuran (320 mL) and water (160 mL) at room temperature. The reaction mixture was stirred at 55° C. overnight. The reaction was concentrated under reduced pressure to remove tetrahydrofuran, acidified to pH˜3 by adding aqueous 1 M HCl while cooling. The precipitate was collected by filtration and dried in a dessicator containing KOH overnight. Recrystallization from heptane afforded the titled compound. MS (ESI+) m/z 227 (M+H)+.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customto remove tetrahydrofuran
  3. additionby adding aqueous 1 M HCl
  4. temperaturewhile cooling
  5. filtrationThe precipitate was collected by filtration
  6. customdried in a dessicator
  7. additioncontaining KOH overnight
  8. customRecrystallization from heptane

Sources & evidence

ORD record
ord-6c9b168afaef440ea99f9842e4f34f65
Source dataset
uspto-grants-2013_08
Patent number
US08507493B2

Reaction notes

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