HCID 6325197, compound → HCID 10867925, compound

HRID 1275696Notes

Reaction equation

HRID 1275696 reaction equation
[OH:1][CH:2]1[C@@H:7]2[C:8]([CH2:11][OH:12])=[CH:9][CH2:10][C@@H:6]2[C:5]([C:13]([O:15][CH3:16])=[O:14])=[CH:4][O:3]1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.CCCCCC.C(OC(=O)C)C>C(Cl)Cl>[CH:11]([C:8]1[C@H:7]2[CH:2]([OH:1])[O:3][CH:4]=[C:5]([C:13]([O:15][CH3:16])=[O:14])[C@H:6]2[CH2:10][CH:9]=1)=[O:12]

Participants

5

Reactant 3

HCID 6325197HCID 6325197, compoundHCID 21226206Ethyl acetate hexaneHCID 178418287HCID 178418287, compound

Product 1

HCID 10867925HCID 10867925, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.5 g (2.21 mmol) of methyl (4aS,7aS)-1-hydroxy-7-hydroxymethyl-1,4a, 5,7a-tetrahydrocyclopenta[c]pyran4carboxylate was dissolved in 10 ml of dried methylene chloride, then 0.954 g (4.42 mmol) of pyridiniumchlorochromate was added thereto. The reaction solution was stirred for 3 hours, filtered through cellite and then the filtrate was concentrated. The residue was subjected to silica gel column chromatography (eluent: n-hexane/ethylacetate=2/1, v/v) to obtain 0.376 g (Yield 76%) of methyl (4aS,7aS)-7-formyl-1-hydroxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate.

Workup

  1. filtrationfiltered through cellite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-6702feafc58f40eb89af14a3c7dc3b89
Source dataset
uspto-grants-2000_12
Patent number
US06162826

Reaction notes

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