Hydrochloric Acid → {2-[4-(3-Chloropropoxy)phenyl]-4-methyl-1,3-thiazol-5-yl}methanol
Reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[S:13][C:14]([C:18](OC)=[O:19])=[C:15]([CH3:17])[N:16]=2)=[CH:8][CH:7]=1.CO.[BH4-].[Li+].Cl.[OH-].[Na+]>O1CCCC1>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[S:13][C:14]([CH2:18][OH:19])=[C:15]([CH3:17])[N:16]=2)=[CH:10][CH:11]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
To a solution of methyl 2-[4-(3-chloropropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylate i105 (6.13 mmol, 1 eq, 2 g) in tetrahydrofuran (60 ml) is added methanol (19.6 mmol, 3.2 eq, 0.8 ml) and lithium borohydride (13.49 mmol, 2.2 eq, 0.29 g). The mixture is stirred at 75° C. overnight. 1 N aqueous hydrogen chloride (2 ml) is added and the mixture is then stirred at room temperature for 1 hour. Then, a 2 M aqueous sodium hydroxide solution is added to reach pH 12 and the mixture is stirred for 6 hours, then extracted twice with ethyl acetate. The organic layer is dried over magnesium sulfate and the solvent is removed under reduced pressure to give 1.65 g of {2-[4-(3-chloropropoxy)phenyl]-4-methyl-1,3-thiazol-5-yl}methanol i109 as a white solid.
Workup
- stirringthe mixture is then stirred at room temperature for 1 hour
- stirringthe mixture is stirred for 6 hours
- extractionextracted twice with ethyl acetate
- dry with materialThe organic layer is dried over magnesium sulfate
- customthe solvent is removed under reduced pressure
Sources & evidence
- ORD record
- ord-f2a9316f815b45efafe7dacd170511fe
- Source dataset
- uspto-grants-2010_09
- Patent number
- US07790720B2
Reaction notes
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