Pyridine → HCID 13194899, compound

HRID 27460Notes

Reaction equation

HRID 27460 reaction equation
N1C=CC=CC=1.[CH3:7][O:8][C:9]1[CH2:13][CH2:12][CH:11]([CH2:14][OH:15])[C:10]=1[C:16]([O:18][CH3:19])=[O:17].CCOCC>C(Cl)Cl>[CH3:7][O:8][C:9]1[CH2:13][CH2:12][CH:11]([CH:14]=[O:15])[C:10]=1[C:16]([O:18][CH3:19])=[O:17]

Participants

5

Reactant 3

HCID 1049PyridineHCID 3283Diethyl EtherHCID 13194898HCID 13194898, compound

Product 1

HCID 13194899HCID 13194899, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-15 °C

Procedure

25.5 g of chromic oxide were added in small fractions at 15° to 20° C. to a solution of 41 ml of pyridine in 400 ml of anhydrous methylene chloride and the mixture was stirred for 15 minutes and was then cooled to -15° C. A solution of 4.3 g of the product of Step G in 10 ml of methylene chloride was added thereto and after 90 minutes, 50 g of celite and 100 ml of ether were added. The mixture was filtered and the filtrate was washed with ether and evaporated to dryness at 30° C. to obtain methyl (5RS) 2-methoxy-5-formyl-1-cyclopentene-carboxylate.

Workup

  1. waitafter 90 minutes
  2. filtrationThe mixture was filtered
  3. washthe filtrate was washed with ether
  4. customevaporated to dryness at 30° C.

Sources & evidence

ORD record
ord-9dcb8e6c3332465cbbb6b331356bddd9
Source dataset
uspto-grants-1980_09
Patent number
US04221809

Reaction notes

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