Acetone → 2-[5-(Tributylstannyl)-1,3-thiazol-2-yl]propan-2-ol
Reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[Li]CCCC.[CH3:11][C:12]([CH3:14])=[O:13].[CH2:15]([Sn:19](Cl)([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH3:18].[NH4+].[Cl-]>C1COCC1.CCOCC>[CH2:24]([Sn:19]([CH2:15][CH2:16][CH2:17][CH3:18])([CH2:20][CH2:21][CH2:22][CH3:23])[C:5]1[S:1][C:2]([C:12]([OH:13])([CH3:14])[CH3:11])=[N:3][CH:4]=1)[CH2:25][CH2:26][CH3:27]Participants
8
Conditions
- Temperature
- -78 °C
Procedure
To a solution of thiazole (1.0 eq) in THF (0.2M) at −78° C. was added nBuLi (1.6M, 1.1 eq). After 1 h at −78° C., acetone (1.0 eq) was added and the mixture stirred 30 min at −78° C., 5 min −50° C. then cooled back to −78° C. to add a second equivalent of nBuLi (1.6M, 1.1 eq). After 1.5 h at −78° C., tri-n-butyltin chloride (1.2 eq) was added and the mixture stirred 12 h at −78° C. The reaction mixture was diluted with Et2O and a solution of NH4Cl. The organic extracts were washed with water, brine, dried over MgSO4, filtered and concentrated. Flash chromatography (Hexane:EtOAc, 90:10) afforded the title compound.
Workup
- temperature5 min −50° C. then cooled back to −78° C.
- waitAfter 1.5 h at −78° C.
- stirringthe mixture stirred 12 h at −78° C
- washThe organic extracts were washed with water, brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-f6ba3af8f1cf4d8f9ace31be503e443d
- Source dataset
- uspto-grants-2009_01
- Patent number
- US07482456B2
Reaction notes
Loading…