Reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[N:14]=2)=[CH:6][CH:5]=1.CC(C[AlH]CC(C)C)C.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>C1COCC1>[S:11]1[C:12]2[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=2[N:14]=[C:10]1[C:7]1[CH:8]=[CH:9][C:4]([CH2:3][OH:2])=[CH:5][CH:6]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
To a 0° C. solution of methyl-4-(benzothiazol-2-yl)-benzoate (prepared as described by A. Brembilla, D. Roizard and P. Lochon Synth. Commun. 1990, 20, 3379) (1.08 g, 4 mmol) in THF (20 mL) was added DIBAL-H (20 mL of a 1.0M solution in THF, 20 mmol) over 10 minutes. The resulting solution was stirred at 0° C. for 2 hours, then an aqueous saturated solution of sodium potassium tartrate was added and the biphasic mixture stirred rapidly for 60 min. The phases were separated and the aqueous layer extracted with ether (3×20 mL). The combined organic fractions were dried (Na2SO4), concentrated and purified by column chromatography on silica gel (10:1 CH2Cl2/MeOH) to afford the title compound (0.69 g, 75%). 1H NMR (CD3OD) δ 4.69 (s, 2H), 7.43 (t, 1H, J=7.8 Hz), 7.53 (m, 3H), 7.99 (m, 1H), 8.06 (m, 3H).
Workup
- stirringthe biphasic mixture stirred rapidly for 60 min
- customThe phases were separated
- extractionthe aqueous layer extracted with ether (3×20 mL)
- dry with materialThe combined organic fractions were dried (Na2SO4)
- concentrationconcentrated
- custompurified by column chromatography on silica gel (10:1 CH2Cl2/MeOH)
Sources & evidence
- ORD record
- ord-95e468a9fa17458cbc976ef761717842
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07091217B2
Linked notes
Loading…