Cornforth reagent → HCID 15053044, compound

HRID 1789560Notes

Reaction equation

HRID 1789560 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]1[CH2:14][CH2:13][CH:12]2[CH:8]1[CH2:9][C:10](=[O:15])[CH2:11]2.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH:7]1[CH2:14][CH2:13][CH:12]2[CH:8]1[CH2:9][C:10](=[O:15])[CH2:11]2)=[O:1]

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 14204106HCID 14204106, compound3×

Product 1

HCID 15053044HCID 15053044, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The procedure followed is the same as that described in Example 13 substituting the starting material prepared in Example 11, 2-(5-hydroxypent-1-yl)bicyclo[3.3.0]octan-7-one {hexahydro-4-(5-hydroxypentyl)-2(1H)-pentalenone} (0.3 g, 1.4 mmoles), and pyridinium dichromate (0.80 g, 2.1 mmoles) dissolved in methylene chloride (5 ml). The crude product is chromatographed on silica gel leaving a clear, colorless oil (0.14 g, 0.67 mmoles).

Sources & evidence

ORD record
ord-4bfd13e2c66f4c80905465f8201f5229
Source dataset
uspto-grants-1987_08
Patent number
US04689345

Reaction notes

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