HCID 54252927, compound → HCID 57227525, compound

HRID 1275695Notes

Reaction equation

HRID 1275695 reaction equation
[OH:1][CH2:2][C:3]1[C@H:7]2[C@H:8]([O:23][CH3:24])[O:9][CH:10]=[C:11]([CH2:12][O:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[C@H:6]2[CH2:5][CH:4]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH:2]([C:3]1[C@H:7]2[C@H:8]([O:23][CH3:24])[O:9][CH:10]=[C:11]([CH2:12][O:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[C@H:6]2[CH2:5][CH:4]=1)=[O:1]

Participants

4

Reactant 2

HCID 54252927HCID 54252927, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 57227525HCID 57227525, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.240 g (0.72 mmol) of (1R,4aS,7aS)-7-hydroxymethyl-1-methoxy4-(p-methoxybenzyloxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran was dissolved in 5 ml of methylene chloride and 0.311 g (1.44 mmol) of pyridiniumchlorochromate was added thereto. The reaction solution was stirred for one hour, filtered through diatomaceous earth, and then concentrated. The residue was subjected to silica gel column chromatography (eluent: n-hexanelethylacetate=4/1, v/v) to obtain 0.167 g (Yield 70%) of (1R,4aS,7aS)-7-formyl-1-methoxy-4-(p-methoxybenzyloxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran as a colorless oil.

Workup

  1. filtrationfiltered through diatomaceous earth
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-4f89b5eef6d14c6287dd8f1badf1672f
Source dataset
uspto-grants-2000_12
Patent number
US06162826

Reaction notes

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