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 the solution was stirred at 0° C. The solution was added dropwise with a solution of (S)-(+)-2,2-dimethyl-1,3-dioxolan-4-methanol (2.4 g) in a mixture of DMF (3 mL) and THF (3 mL), and stirred at 0° C. for one hour. The solution was added with 4-methoxybenzyl chloride (2.8 mL), and stirred at room temperature for 3 hours. The solution was added with saturated ammonium chloride, and extracted twice with ethyl acetate. The resulting organic layer was washed four times with water and ones with saturated brine. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was removed to obtain a crude product of (S)-(+)-4-(4-methoxybenzyloxymethyl)-2,2-dimethyl-1,3-dioxolane (4.1 g, 89%).
Workup
- stirringstirred at 0° C. for one hour
- stirringstirred at room temperature for 3 hours
- extractionextracted twice with ethyl acetate
- washThe resulting organic layer was washed four times with water and ones with saturated brine
- dry with materialAfter the organic layer was dried over anhydrous magnesium sulfate
- customthe solvent was removed
Sources & evidence
- ORD record
- ord-f1862217fe0b4fd1b255891c70ee37c3
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07887835B2
Reaction notes
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