Reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([CH2:11][C:12]1[S:13][CH:14]=[CH:15][C:16]=1[C:17](OC)=[O:18])=O.O.[OH-].[Na+]>O1CCCC1>[OH:18][CH2:17][C:16]1[CH:15]=[CH:14][S:13][C:12]=1[CH2:11][CH2:9][OH:8]Participants
Procedure
In a dried vessel, 600 mg of lithium aluminum hydride was charged under a nitrogen atmosphere, and then 26 mL of anhydrous tetrahydrofuran was added thereto. To the resulting suspension, a solution of 2.8 g of the compound obtained in Example 1 dissolved in 10 mL of tetrahydrofuran was added over about 5 minutes. The resulting mixture was stirred at room temperature for 1 hour, and then refluxed for 1 hour. The reaction solution was cooled to 0° C., and 0.5 mL of water, 0.5 mL of 15% sodium hydroxide aqueous solution, and 4 mL of water were added thereto slowly in succession. The resulting mixture was stirred for about 1 hour, and the insoluble materials was filtered and washed with 30 mL of tetrahydrofuran. Combined filtrate was concentrated by evaporation under reduced pressure to obtain 1.8 g (yield of 87%) of oily title compound.
Workup
- additionwas added over about 5 minutes
- temperaturerefluxed for 1 hour
- temperatureThe reaction solution was cooled to 0° C.
- stirringThe resulting mixture was stirred for about 1 hour
- filtrationthe insoluble materials was filtered
- washwashed with 30 mL of tetrahydrofuran
- concentrationCombined filtrate was concentrated by evaporation under reduced pressure
Sources & evidence
- ORD record
- ord-2cdc5d8640f14ccdbca4f7b166295c52
- Source dataset
- uspto-grants-2008_11
- Patent number
- US07449580B2
Linked notes
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