2-Phenylethanol → 2-[4-(6-Methyl-benzothiazol-2-yloxy)-phenyl]-ethanol
Reaction equation
[CH2:1]([OH:9])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:10]([O-:13])([O-])=O.[K+].[K+].ClC1[S:18][C:19]2[CH:25]=[C:24]([CH3:26])[CH:23]=[CH:22][C:20]=2[N:21]=1.[OH-].[Na+].C(OC(C)C)(=O)C>CC#N>[CH3:26][C:24]1[CH:23]=[CH:22][C:20]2[N:21]=[C:10]([O:13][C:6]3[CH:7]=[CH:8][C:3]([CH2:2][CH2:1][OH:9])=[CH:4][CH:5]=3)[S:18][C:19]=2[CH:25]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a solution of phenethyl alcohol (3.15 g, 22.86 mmol) and K2CO3 (5.26 g, 38.1 mmol) in CH3CN (35 mL) was added 2-chloro-6-methylbenzothiazole (3.5 g, 19.1 mmol). The reaction mixture was heated at 80° C. for 16 h. To the reaction mixture was added 1 N NaOH (30 mL) and isopropyl acetate (40 mL). The layers were separated and the aqueous layer was extracted with isopropyl acetate (2×30 mL). The combined organic layers were dried (Na2SO4), filtered and concentrated. The resulting residue was purified by silica gel flash chromatography (20% to 90% EtOAc in hexanes) to afford the title compound (3.4 g, 63%). 1H NMR (500 MHz, CDCl3): 7.61 (d, J=8.3 Hz, 1H), 7.47 (s, 1H), 7.33-7.28 (m, 4H), 7.20 (d, J=8.3 Hz, 1H), 3.87 (br s, 2H), 2.90 (t, J=6.6 Hz, 2H), 2.44 (s, 3H).
Workup
- customThe layers were separated
- extractionthe aqueous layer was extracted with isopropyl acetate (2×30 mL)
- dry with materialThe combined organic layers were dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
- customThe resulting residue was purified by silica gel flash chromatography (20% to 90% EtOAc in hexanes)
Sources & evidence
- ORD record
- ord-1d8731fc68e3457d9a984917cf0301ac
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08367719B2
Reaction notes
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