(E)-3-((1RS,2SR,4SR)-2-methyl-3-methylenebicyclo[2.2.1]hept-5-en-2-yl)acrylaldehyde → HCID 15599971, compound

HRID 71065Notes

Reaction equation

HRID 71065 reaction equation
[CH3:1][C:2]1(/[CH:10]=[CH:11]/[CH:12]=[O:13])[C:7](=[CH2:8])[CH:6]2[CH2:9][CH:3]1[CH:4]=[CH:5]2>CCO.O.[Ni]>[CH3:1][C:2]1([CH2:10][CH2:11][CH:12]=[O:13])[C:7](=[CH2:8])[CH:6]2[CH2:9][CH:3]1[CH2:4][CH2:5]2

Participants

4

Reactant 1

HCID 89904621(E)-3-((1RS,2SR,4SR)-2-methyl-3-methylenebicyclo[2.2.1]hept-5-en-2-yl)acrylaldehyde

Product 1

HCID 15599971HCID 15599971, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 19096565Water ethanolSolvent

Procedure

Obtained in 85% yield by hydrogenation of 23 (2.0-mol-equiv. of H2) over Raney-Ni (5% by weight) at 0° in EtOH/H2O 95:5. (90% based on the recovered SM). For analyses, see H. Sonawane, R. Harikisan, N. S. Bellur, J. R. Ahuja, D. J. Kulkarni, J. Org. Chem. 1991, 56, 1434; M. Saito, M. Kawamura, K. Ogasawara, Tetr. Lett. 1995, 36, 9003; D. Solas, J. Wolinsky, J. Org. Chem. 1983, 48, 1988; P. A. Christenson, B. J. Willis, J. Org. Chem. 1979, 44, 2012.

Sources & evidence

ORD record
ord-d33f4b207d6742c5a72fcb4c21caafaf
Source dataset
uspto-grants-2014_09
Patent number
US08822733B2

Reaction notes

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