Water → HCID 57682874, compound
Reaction equation
CC[C@@H]1[C@@H]2C[C@H]([C@@H](OC3C4C(=CC=CC=4)C(O[C@@H](C4C=CN=C5C=4C=C(OC)C=C5)[C@@H]4N5C[C@H](CC)[C@@H](CC5)C4)=NN=3)C3C=CN=C4C=3C=C([O:22]C)C=C4)N(CC2)C1.[CH2:59]([C:62]1[C:71]([O:72][CH3:73])=[CH:70][CH:69]=[C:68]2[C:63]=1[CH2:64][CH2:65][C:66]([CH3:76])([CH3:75])[C:67]2=[O:74])[CH:60]=[CH2:61].C(O)(C)(C)C.S([O-])([O-])=O.[Na+].[Na+].[OH2:88]>>[OH:88][CH:60]([CH2:61][OH:22])[CH2:59][C:62]1[C:71]([O:72][CH3:73])=[CH:70][CH:69]=[C:68]2[C:63]=1[CH2:64][CH2:65][C:66]([CH3:76])([CH3:75])[C:67]2=[O:74]Participants
Procedure
4.47 g of AD-mix-β was added to a mixture consisting of 1.09 g of 5-allyl-6-methoxy-2,2-dimethyl-3,4-dihydronaphthalen-1(2H)-one, 17 ml of tert-butanol, and 17 ml of water. The obtained mixture was stirred at room temperature overnight. Thereafter, 5.37 g of sodium sulfite was added to the reaction solution, and the obtained mixture was stirred for 35 minutes, followed by extraction with ethyl acetate. The obtained organic layer was washed with a saturated sodium chloride solution and then dried over anhydrous sodium sulfate. After removing the drying agent by filtration, the reaction solution was concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/methanol), so as to obtain 1.25 g of the subject compound.
Workup
- stirringthe obtained mixture was stirred for 35 minutes
- extractionfollowed by extraction with ethyl acetate
- washThe obtained organic layer was washed with a saturated sodium chloride solution
- dry with materialdried over anhydrous sodium sulfate
- customAfter removing the drying agent
- filtrationby filtration
- concentrationthe reaction solution was concentrated under a reduced pressure
- customThe residue was purified by silica gel column chromatography (ethyl acetate/methanol)
Sources & evidence
- ORD record
- ord-df36c9669f6545458b53d2f4a183ffc3
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07538123B2
Reaction notes
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