Toluene → Methyl 2-methyl-2-mesyloxymethyl-3-(4-chlorophenyl)-3-keto-propanoate
Reaction equation
[CH3:1][C:2]([CH2:16][OH:17])([C:7]([C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)=[O:8])[C:3]([O:5][CH3:6])=[O:4].C(N(CC)CC)C.C1(C)C=CC=CC=1.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>C(Cl)Cl.O>[CH3:1][C:2]([CH2:16][O:17][S:33]([CH3:32])(=[O:35])=[O:34])([C:7]([C:9]1[CH:10]=[CH:11][C:12]([Cl:15])=[CH:13][CH:14]=1)=[O:8])[C:3]([O:5][CH3:6])=[O:4]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -10 °C
Procedure
Into a 5 liter RBF is placed 100 g (4.37 mole) of methyl 2-methyl-2-hydroxymethyl-3-(4-chlorophenyl)-3-keto-propanoate, 473 g (4.25 mole) of triethylamine, and 2 liters of toluene. This mixture is cooled to -10° C. and methane sulfonyl chloride, 488 g (4.25 mole), is added over 30 minutes. The internal temperature rose to 40° C. by the end of the addition. After stirring at room temperature for 2 hours, the mixture is worked up with 4 liters of cold water and 1 liter methylene chloride. The resulting red semisolid (1400 g) is crystalized using 200 ml of hot ethyl acetate and adding 1500 ml of hexane. Yielding 1060 g (74%) of a light yellow solid mp 85°-86° C., methyl 2-methyl-2-mesyloxymethyl-3-(4-chlorophenyl)-3-keto-propanoate. NMR data was consistent with the structure.
Workup
- additionThe internal temperature rose to 40° C. by the end of the addition
- customThe resulting red semisolid (1400 g) is crystalized
- additionadding 1500 ml of hexane
Sources & evidence
- ORD record
- ord-103cee6d9c124303ae5524bc607ef47a
- Source dataset
- uspto-grants-1989_09
- Patent number
- US04863947
Reaction notes
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