Aluminium lithium hydride → 2-(2,4-bis-benzyloxy-5-isopropyl-benzoyl)-2,3-dihydro-1H-isoindole-5-carbaldehyde

HRID 2355748Notes

Reaction equation

HRID 2355748 reaction equation
CON(C)[C:4]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[CH2:11][N:10]([C:15](=[O:41])[C:16]1[CH:21]=[C:20]([CH:22]([CH3:24])[CH3:23])[C:19]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:18][C:17]=1[O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH2:9]2)=[O:5].[H-].[H-].[H-].[H-].[Li+].[Al+3].C1COCC1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:34]([O:33][C:17]1[CH:18]=[C:19]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:20]([CH:22]([CH3:24])[CH3:23])=[CH:21][C:16]=1[C:15]([N:10]1[CH2:9][C:8]2[C:12](=[CH:13][CH:14]=[C:6]([CH:4]=[O:5])[CH:7]=2)[CH2:11]1)=[O:41])[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

5

Reactant 3

HCID 21226445Aluminium lithium hydrideHCID 469151852-(2,4-bis-benzyloxy-5-isopropyl-benzoyl)-2,3-dihydro-1H-isoindole-5-carboxylic acid methoxy-methyl-amideHCID 68718528lithium aluminium hydride THF

Product 1

HCID 469150232-(2,4-bis-benzyloxy-5-isopropyl-benzoyl)-2,3-dihydro-1H-isoindole-5-carbaldehydeYield 98.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(2,4-bis-benzyloxy-5-isopropyl-benzoyl)-2,3-dihydro-1H-isoindole-5-carboxylic acid methoxy-methyl-amide (0.226 g, 0.4 mmol) in THF (5 ml) cooled to 0° C., treated with 1M LiAlH4/THF (0.3 ml, 0.3 mmol), stirred 1 hour, further LiAlH4 (0.05 ml) added then stirred for 30 minutes. The reaction was quenched with saturated KHSO4 solution, extracted with EtOAc, dried (MgSO4), filtered and evaporated to give 0.2 g of 2-(2,4-bis-benzyloxy-5-isopropyl-benzoyl)-2,3-dihydro-1H-isoindole-5-carbaldehyde. MS: [M+H]+ 504

Workup

  1. stirringthen stirred for 30 minutes
  2. customThe reaction was quenched with saturated KHSO4 solution
  3. extractionextracted with EtOAc
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-f7978c9a6b35466ab08d4f2a9580d4eb
Source dataset
uspto-grants-2010_07
Patent number
US07754725B2

Reaction notes

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