HCID 12967234, compound → HCID 11076774, compound

HRID 324174Notes

Reaction equation

HRID 324174 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[CH2:6][O:7][CH2:8][C:9]([CH3:17])([CH3:16])[CH:10]([OH:15])[C:11]([CH3:14])([CH3:13])[CH3:12].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[CH2:6][O:7][CH2:8][C:9]([CH3:17])([CH3:16])[C:10](=[O:15])[C:11]([CH3:13])([CH3:14])[CH3:12]

Participants

4

Reactant 2

HCID 12967234HCID 12967234, compound2×HCID 178418287HCID 178418287, compound2×

Product 1

HCID 11076774HCID 11076774, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In nitrogen atmosphere at a room temperature, 9.9 g of Celite and 4.61 g (16.5 mmol) of 1-(3-methoxybenzyloxy)-2,2,4,4-tetramethyl-3-pentanol (Compound [48]) were added to 75 ml of dichloromethane and the mixture was stirred. After adding 4.26 g (19.7 mmol) of PCC and stirring for 7 hours, 800 mg (3.71 mmol) of PCC was added and then the reaction mixture was stirred over night. Adding ether to the reaction mixture, the resulting mixture was filtrated by Celite and the filtrate was concentrated. The concentrate was applied to a silica gel column and the elution was carried out with the mixture of hexane and ethyl acetate (hexane:ethyl acetate=10:1) to obtain 4.32 g of 1-(3-methoxybenzyloxy)-2,2,4,4-tetramethyl-3-pentanon (Compound [49]) as a colorless compound. Yield 94.4%.

Workup

  1. stirringstirring for 7 hours
  2. stirringthe reaction mixture was stirred over night
  3. filtrationAdding ether to the reaction mixture, the resulting mixture was filtrated by Celite
  4. concentrationthe filtrate was concentrated
  5. washthe elution
  6. additionwas carried out with the mixture of hexane and ethyl acetate (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-e39bfe6088d44290bb0a4e80aa80e962
Source dataset
uspto-grants-2001_04
Patent number
US06218135B1

Reaction notes

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