Triethylamine → 1,1-Dimethoxy-1-(6-methoxy-2-naphthyl)prop-2-yl methanesulfonate
Reaction equation
[CH3:1][O:2][C:3]([O:19][CH3:20])([C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17][CH3:18])[CH:13]=2)[CH:8]=1)[CH:4]([OH:6])[CH3:5].C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30].Cl.C(N(CC)CC)C>C1(C)C=CC=CC=1.O>[CH3:28][S:29]([O:6][CH:4]([CH3:5])[C:3]([O:19][CH3:20])([O:2][CH3:1])[C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17][CH3:18])[CH:13]=2)[CH:8]=1)(=[O:31])=[O:30]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 10 °C
Procedure
The oil, 1,1-dimethoxy-1-(6-methoxy-2-naphthyl)-propan-2-ol, prepared in Example 15 is dissolved in 200 ml of toluene, cooled to about 10° C., and to that solution is added 10.5 g of triethylamine. Then 8.5 g of methanesulfonyl chloride is added dropwise to the solution and an exothermic reaction is noted along with the precipation of triethylamine hydrochloride crystals. The addition occurs over about a 45 minute period and the solution is allowed to warm to about 20° C. Then the reaction mixture is poured into water and extracted with toluene-ether. The organic extracts are separated, dried over magnesium sulfate and evaporated to yield 1,1-dimethoxy-1-(6-methoxy-2-naphthyl)prop-2-yl methanesulfonate as an oil.
Workup
- customan exothermic reaction
- additionThe addition
- customoccurs over about a 45 minute period
- temperatureto warm to about 20° C
- extractionextracted with toluene-ether
- customThe organic extracts are separated
- dry with materialdried over magnesium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-cf8fb0eb21b1427997acbe6a87d02979
- Source dataset
- uspto-grants-1987_03
- Patent number
- US04654438
Reaction notes
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