Benzene → HCID 11286510, compound

HRID 842439Notes

Reaction equation

HRID 842439 reaction equation
I[C@@H:2]1[C@@H:8]2[CH2:9][C@@H:5]([C:6](=[O:10])[O:7]2)[C@H:4]([CH3:11])[CH2:3]1.[SnH](CCCC)(CCCC)CCCC.CC(N=NC(C#N)(C)C)(C#N)C.C1C=CC=CC=1>[Ni].N1C=CC=CC=1>[CH3:11][C@@H:4]1[CH2:3][CH2:2][C@@H:8]2[CH2:9][C@H:5]1[C:6](=[O:10])[O:7]2

Participants

7

Reactant 4

HCID 241BenzeneHCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 11323077HCID 11323077, compound

Product 1

HCID 11286510HCID 11286510, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 1049PyridineSolvent

Procedure

reacting said (1R,2R,4S,5S)-4-iodo-2-methyl-6-oxabicyclo[3.2.1]octan-7-one (8) with n-Bu3SnH and catalytic AIBN in refluxing benzene, or with Raney Nickel in the presence of pyridine under 50 psi H2, to produce (1R,2R,5R)-2-methyl-6-oxabicyclo[3.2.1]octan-7-one (9),

Sources & evidence

ORD record
ord-ec9ea23b0ef04726acf41f3e935a7100
Source dataset
uspto-grants-2002_04
Patent number
US06375943B1

Reaction notes

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