Aluminium lithium hydride → HCID 11097747, compound

HRID 1795109Notes

Reaction equation

HRID 1795109 reaction equation
CON(C)[C:4](=[O:22])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)(=[O:14])=[O:13].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1.CCOC(C)=O>[CH3:21][C:18]1[CH:17]=[CH:16][C:15]([S:12]([CH2:11][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH:4]=[O:22])(=[O:14])=[O:13])=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22185694HCID 22185694, compound

Product 1

HCID 11097747HCID 11097747, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-methoxy-N-methyl-2-{[(4-methylphenyl)sulfonyl]methyl}benzamide (0.645 mmol) in 5 mL THF at −78° C. is added 1.0 M solution of LiAlH4 in THF (0.709 mmol) slowly with stirring. The reaction is stirred at −78° C. for 1 hr and gradually warmed up to RT. The reaction mixture is diluted with EtOAc and washed with H2O. The solution is dried over Na2SO4 and the solvent is evaporated to give a quantitative yield of 2-{[(4-methylphenyl)sulfonyl]methyl}benzaldehyde.

Workup

  1. stirringThe reaction is stirred at −78° C. for 1 hr
  2. washwashed with H2O
  3. dry with materialThe solution is dried over Na2SO4
  4. customthe solvent is evaporated

Sources & evidence

ORD record
ord-81deff12ad324fbbbcb4fc777a9c9c48
Source dataset
uspto-grants-2006_04
Patent number
US07026339B2

Reaction notes

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