Cornforth reagent → 4-[7-(1-Adamantyl)-6-methoxyethoxymethoxy-2-naphthyl]benzaldehyde
Reaction equation
[C:1]12([C:11]3[CH:20]=[C:19]4[C:14]([CH:15]=[CH:16][C:17]([C:21]5[CH:26]=[CH:25][C:24]([CH2:27][OH:28])=[CH:23][CH:22]=5)=[CH:18]4)=[CH:13][C:12]=3[O:29][CH2:30][O:31][CH2:32][CH2:33][O:34][CH3:35])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>ClCCl>[C:1]12([C:11]3[CH:20]=[C:19]4[C:14]([CH:15]=[CH:16][C:17]([C:21]5[CH:26]=[CH:25][C:24]([CH:27]=[O:28])=[CH:23][CH:22]=5)=[CH:18]4)=[CH:13][C:12]=3[O:29][CH2:30][O:31][CH2:32][CH2:33][O:34][CH3:35])[CH2:10][CH:5]3[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]3)[CH2:8]1)[CH2:2]2Participants
4
Procedure
2.63 g (5.9 mmol) of 4-[7-(1-adamantyl)-6-methoxyethoxymethoxy-2-naphthyl]benzenemethanol and 40 ml of dichloromethane were introduced into a round-bottomed flask and 4.2 g of pyridinium dichromate were added. The reaction mixture was stirred at room temperature for twelve hours, was filtered through silica and the filtrate was evaporated. The solid obtained was recrystallized from heptane and 490 mg (19%) of 4-[7-(1-adamantyl)-6-methoxyethoxymethoxy-2-naphthyl]benzaldehyde were collected, which compound had a melting point of 83°-4° C.
Workup
- filtrationwas filtered through silica
- customthe filtrate was evaporated
- customThe solid obtained
- customwas recrystallized from heptane and 490 mg (19%) of 4-[7-(1-adamantyl)-6-methoxyethoxymethoxy-2-naphthyl]benzaldehyde
- customwere collected
Sources & evidence
- ORD record
- ord-7e07f65eded84615aa0932039bd2f172
- Source dataset
- uspto-grants-2001_05
- Patent number
- US06225328B1
Reaction notes
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