Cornforth reagent → HCID 22120168, compound

HRID 1274104Notes

Reaction equation

HRID 1274104 reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[CH3:22][C:23]1([CH3:48])[CH2:32][CH2:31][C:30]([CH3:34])([CH3:33])[C:29]2[CH:28]=[C:27]([O:35][C:36]3[CH:37]=[C:38]4[C:43](=[CH:44][CH:45]=3)[C:42]([CH2:46][OH:47])=[CH:41][CH:40]=[CH:39]4)[CH:26]=[CH:25][C:24]1=2>ClCCl>[CH3:22][C:23]1([CH3:48])[CH2:32][CH2:31][C:30]([CH3:33])([CH3:34])[C:29]2[CH:28]=[C:27]([O:35][C:36]3[CH:37]=[C:38]4[C:43](=[CH:44][CH:45]=3)[C:42]([CH:46]=[O:47])=[CH:41][CH:40]=[CH:39]4)[CH:26]=[CH:25][C:24]1=2

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 22120170HCID 22120170, compound

Product 1

HCID 22120168HCID 22120168, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

100 ml of dichloromethane and 1.7 g (4.5 mmol) of pyridinium dichromate were introduced into a round-bottomed flask. The mixture was cooled to 0° C. and a solution of 1.2 g (3.3 mmol) of 6-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyloxy)naphthalene methanol in 20 ml of dichloromethane was added dropwise. The mixture was stirred at room temperature for one hour, the reaction medium was filtered over silica, the filtrate was evaporated to dryness and the solid was triturated in heptane and filtered off. 1.07 g (90%) of the expected aldehyde was recovered, having a melting point of 123°-4° C.

Workup

  1. filtrationthe reaction medium was filtered over silica
  2. customthe filtrate was evaporated to dryness
  3. customthe solid was triturated in heptane
  4. filtrationfiltered off
  5. custom1.07 g (90%) of the expected aldehyde was recovered

Sources & evidence

ORD record
ord-d44cc47d87e84665a65a6a4ba23df448
Source dataset
uspto-grants-2000_12
Patent number
US06156750

Reaction notes

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