Sodium Sulfite → 8-(2,3-Dihydroxypropyl)-7-methoxy-2,2-dimethyl-4-oxochroman
Reaction equation
[CH2:1]([C:4]1[C:5]([O:17][CH3:18])=[CH:6][CH:7]=[C:8]2[C:13]=1[O:12][C:11]([CH3:15])([CH3:14])[CH2:10][C:9]2=[O:16])[CH:2]=[CH2:3].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:40]C)C=C4)N(CC2)C1.S([O-])([O-])=O.[Na+].[Na+].C(O)(C)(C)C.[OH2:88]>C(OCC)(=O)C>[OH:88][CH:2]([CH2:3][OH:40])[CH2:1][C:4]1[C:5]([O:17][CH3:18])=[CH:6][CH:7]=[C:8]2[C:13]=1[O:12][C:11]([CH3:14])([CH3:15])[CH2:10][C:9]2=[O:16]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
126 mg of 8-allyl-7-methoxy-2,2-dimethyl-4-oxochroman was dissolved in 12 ml of t-butanol-water (1:1) under nitrogen atmosphere. Thereafter, 0.72 g of AD-mix-β was added to the reaction solution, and the obtained mixture was then stirred at room temperature for 24 hours. Thereafter, 0.77 g of sodium sulfite was added to the reaction solution while cooling on ice, and the obtained mixture was stirred at room temperature for 1 hour. The reaction solution was diluted with ethyl acetate, and then washed with a saturated sodium chloride aqueous solution. The organic layer was dried over magnesium sulfate and then filtered. The organic layer was then concentrated under a reduced pressure, so as to obtain 145 mg of 8-(2,3-dihydroxypropyl)-7-methoxy-2,2-dimethyl-4-oxochroman. This compound was used in the following reaction without further purification.
Workup
- temperaturewhile cooling on ice
- stirringthe obtained mixture was stirred at room temperature for 1 hour
- washwashed with a saturated sodium chloride aqueous solution
- dry with materialThe organic layer was dried over magnesium sulfate
- filtrationfiltered
- concentrationThe organic layer was then concentrated under a reduced pressure
Sources & evidence
- ORD record
- ord-da6278867193423bbfe4cab35c35ffab
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07538123B2
Reaction notes
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