Cornforth reagent → HCID 15053044, compound

HRID 1722383Notes

Reaction equation

HRID 1722383 reaction equation
OCCCCCC12CC(=O)CC1CCC2.[OH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH:22]1[CH2:29][CH2:28][CH:27]2[CH:23]1[CH2:24][C:25](=[O:30])[CH2:26]2.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH:17]([CH2:18][CH2:19][CH2:20][CH2:21][CH:22]1[CH2:29][CH2:28][CH:27]2[CH:23]1[CH2:24][C:25](=[O:30])[CH2:26]2)=[O:16]

Participants

5

Reactant 3

HCID 2724130Cornforth reagentHCID 14204106HCID 14204106, compoundHCID 20028720HCID 20028720, compound2×

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-d2b3475f97814994a50ad7e32bf3d986
Source dataset
uspto-grants-1989_08
Patent number
US04855322

Reaction notes

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