Sodium Hydroxide → HCID 59497761, compound

HRID 1024388Notes

Reaction equation

HRID 1024388 reaction equation
C[O:2][C:3]([C:5]1([C:11]2[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=2)[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>C1COCC1>[Br:17][C:14]1[CH:15]=[CH:16][C:11]([C:5]2([CH2:3][OH:2])[CH2:10][CH2:9][O:8][CH2:7][CH2:6]2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 59497758HCID 59497758, compound

Product 1

HCID 59497761HCID 59497761, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of intermediate D9 (1.07 g, 3.58 mmol) in THF (20 ml) stirred at −10° C. under N2 atmosphere, was added a 1.0 M solution of lithium aluminum hydride in THF dropwise (3.58 ml, 3.58 mmol). The resulting solution was gradually warmed to room temperature and further stirred for 2 hours. After cooling to 0° C. an aqueous 10% NaOH solution was carefully added and the resulting mixture was allowed to reach room temperature. Then it was extracted with DCM, dried (Na2SO4) and the solvent evaporated in vacuo to yield intermediate D10 (0.96 g, 99%) as a white solid that was used without further purification.

Workup

  1. additionwas carefully added
  2. customto reach room temperature
  3. extractionThen it was extracted with DCM
  4. dry with materialdried (Na2SO4)
  5. customthe solvent evaporated in vacuo
  6. customto yield intermediate D10 (0.96 g, 99%) as a white solid that
  7. customwas used without further purification

Sources & evidence

ORD record
ord-90291f559315454b87f61b3b234362e0
Source dataset
uspto-grants-2014_05
Patent number
US08722894B2

Reaction notes

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