Lithium hydroxide, monohydrate → HCID 86646145, compound

HRID 551675Notes

Reaction equation

HRID 551675 reaction equation
O.[OH-].[Li+].[Si:4]([O:11][CH2:12][CH:13]([CH2:20][CH:21]=[CH2:22])/[CH:14]=[CH:15]/[C:16]([O:18]C)=[O:17])([C:7]([CH3:10])([CH3:9])[CH3:8])([CH3:6])[CH3:5]>O1CCCC1.CO.O>[Si:4]([O:11][CH2:12][CH:13]([CH2:20][CH:21]=[CH2:22])/[CH:14]=[CH:15]/[C:16]([OH:18])=[O:17])([C:7]([CH3:10])([CH3:9])[CH3:8])([CH3:5])[CH3:6]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86646144HCID 86646144, compound

Product 1

HCID 86646145HCID 86646145, compound

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Lithium hydroxide monohydrate (2.52 g, 60.0 mmol) was added to a tetrahydrofuran:methanol:water (3:1:1, 100 mL) mixed solution of methyl (2E)-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)hepta-2,6-dienoate (5.69 g, 20.0 mmol), and the mixture was stirred at room temperature for 6 hours. The reaction solution was concentrated under reduced pressure. To the residue, water was then added, followed by extraction with methylene chloride. The aqueous layer was made acidic by the addition of 10% hydrochloric acid, followed by extraction with methylene chloride again. Then, the combined organic layers were dried over anhydrous sodium sulfate. The residue was filtered and concentrated under reduced pressure. Then, the obtained crude product was purified by silica gel column chromatography to obtain the compound of interest as an oil substance (3.11 g, 57%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionTo the residue, water was then added
  3. extractionfollowed by extraction with methylene chloride
  4. additionThe aqueous layer was made acidic by the addition of 10% hydrochloric acid
  5. extractionfollowed by extraction with methylene chloride again
  6. dry with materialThen, the combined organic layers were dried over anhydrous sodium sulfate
  7. filtrationThe residue was filtered
  8. concentrationconcentrated under reduced pressure
  9. customThen, the obtained crude product
  10. customwas purified by silica gel column chromatography
  11. customto obtain the compound of interest as an oil substance (3.11 g, 57%)

Sources & evidence

ORD record
ord-7917f52e2cb0448ba05a145594bd3aa6
Source dataset
uspto-grants-2011_05
Patent number
US07947738B2

Reaction notes

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