Water → 3-Cyanohexahydro-2-oxo-3,5-methano-2H-cyclopenta[b]furan-6-yl 2-methyl-2-propenoate
Reaction equation
[C:1]([C:3]12[CH2:11][CH:8]3[CH2:9][CH:10]1[CH:6]([CH:7]3[OH:12])[O:5][C:4]2=[O:13])#[N:2].C(N(CC)CC)C.[C:21](Cl)(=[O:25])[C:22]([CH3:24])=[CH2:23].O>O1CCCC1.C1(C=CC(O)=CC=1)O>[C:1]([C:3]12[CH2:11][CH:8]3[CH2:9][CH:10]1[CH:6]([CH:7]3[O:12][C:21](=[O:25])[C:22]([CH3:24])=[CH2:23])[O:5][C:4]2=[O:13])#[N:2]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 5 °C
Procedure
In 252 g of tetrahydrofuran (THF) was dissolved 23 g (in terms of 0.127 mol) of the above-prepared compound represented by Formula (2a) (crude product). The solution was combined with 16.9 g of triethylamine and 0.2 g of hydroquinone and was further combined with 18.3 g of methacryloyl chloride (3a) added dropwise while cooling the mixture to 5° C. The reaction mixture was combined with 300 ml of water and was extracted with ethyl acetate. The organic layer was sequentially washed with an aqueous sodium hydrogen carbonate solution and water, was concentrated, the concentrate was crystallized from diisopropyl ether and thereby yielded 14 g of 1-cyano-5-methacryloyloxy-3-oxatricyclo[4.2.1.04,8]nonan-2-one represented by Formula (1a).
Workup
- additionadded dropwise
- extractionwas extracted with ethyl acetate
- washThe organic layer was sequentially washed with an aqueous sodium hydrogen carbonate solution and water
- concentrationwas concentrated
- customthe concentrate was crystallized from diisopropyl ether
Sources & evidence
- ORD record
- ord-8be2da4f49514a999c2a31115ee0afff
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08236971B2
Reaction notes
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