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

HRID 41452

Reaktionsgleichung

Reaktionsgleichung von HRID 41452
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

Komponenten

5

Edukt 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

Produkt 1

HCID 469150232-(2,4-bis-benzyloxy-5-isopropyl-benzoyl)-2,3-dihydro-1H-isoindole-5-carbaldehydeAusbeute 98,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-44a8afd05ac247b181fc8f549de2b057
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530469B2

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