Cornforth reagent → 4-[7-(1-Adamantyl)-6-methoxyethoxymethoxy-2-naphthyl]benzaldehyde

HRID 618500Notes

Reaction equation

HRID 618500 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]2

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 702291984-[7-(1-Adamantyl)-6-methoxyethoxymethoxy-2-naphthyl]benzenemethanol

Product 1

HCID 882212364-[7-(1-Adamantyl)-6-methoxyethoxymethoxy-2-naphthyl]benzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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

  1. filtrationwas filtered through silica
  2. customthe filtrate was evaporated
  3. customThe solid obtained
  4. customwas recrystallized from heptane and 490 mg (19%) of 4-[7-(1-adamantyl)-6-methoxyethoxymethoxy-2-naphthyl]benzaldehyde
  5. customwere collected

Sources & evidence

ORD record
ord-38288db0460d48a2b1a710a2976f1a28
Source dataset
uspto-grants-1999_09
Patent number
US05952382

Reaction notes

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