Sodium hydride → HCID 13904786, compound
Reaction equation
[H-].[Na+].[CH3:3][C:4]1([CH3:11])[O:8][C@@H:7]([CH2:9][OH:10])[CH2:6][O:5]1.[CH3:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Cl)=[CH:16][CH:15]=1.[Cl-].[NH4+]>CN(C=O)C.O1CCCC1>[CH3:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][O:10][CH2:9][C@H:7]2[CH2:6][O:5][C:4]([CH3:11])([CH3:3])[O:8]2)=[CH:16][CH:15]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
Sodium hydride (0.8 g) was added with DMF (5 mL) and tetrahydrofuran (THF, 20 mL) and stirred at 0° C. The reaction solution was added dropwise with a solution of (S)-(+)-2,2-dimethyl-1,3-dioxolane-4-methanol (2.4 g) in a mixture of DMF (3 mL) and THF (3 mL) and stirred at 0° C. for 1 hour. The reaction solution was added with 4-methoxybenzyl chloride (2.8 mL) and stirred at room temperature for 3 hours. The reaction solution was added with a saturated ammonium chloride solution and extracted twice with ethyl acetate, and the resulting organic layer was washed four times with water and once with saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed to obtain a crude product of (S)-(+)-4-(4-methoxybenzyloxymethyl)-2,2-dimethyl-1,3-dioxolane (4.1 g, yield: 89%).
Workup
- stirringstirred at 0° C. for 1 hour
- stirringstirred at room temperature for 3 hours
- extractionextracted twice with ethyl acetate
- washthe resulting organic layer was washed four times with water
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- customthe solvent was removed
Sources & evidence
- ORD record
- ord-2a0ee7b72755415a8c85c2d6ae4df61e
- Source dataset
- uspto-grants-2008_05
- Patent number
- US07371877B2
Reaction notes
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