Diethyl Ether → HCID 69507241, compound
Reaction equation
[Cl:1][C:2]([Cl:19])([Cl:18])[CH2:3][O:4][C:5]([O:7][CH2:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[CH2:17])C=O)[N:13]=1)=[O:6].[CH3:20][CH2:21][CH2:22]CC.[C:25]([O-:28])(O)=O.[Na+].[CH3:30]COCC>>[OH:28][C@H:25]([C:17]([CH3:30])=[CH:14][C:12]1[N:13]=[C:9]([CH2:8][O:7][C:5]([O:4][CH2:3][C:2]([Cl:1])([Cl:18])[Cl:19])=[O:6])[S:10][CH:11]=1)[CH2:22][CH:21]=[CH2:20]Participants
Conditions
- Temperature
- -50 °C
Procedure
A solution of 2-methyl-3-(2-((2,2,2-trichloroethoxycarbonyloxymethyl)thiazol-4-yl)propenal (9.20 g) in 50 mL of anhydrous ether is cooled to −100° C. A pentane solution of (+)-diisopinocampheylallylborane (1.5 equiv) is added dropwise to the vigorously stirred aldehyde solution. After the addition is complete, the reaction mixture is stirred for 1.5 hours and warmed to −50° C. A solution of 30% aq H202 (20 mL) and 10% aq NaHCO3 (50 mL) is added, and the resulting turbid mixture is stirred at 25° C. for 8 hours. The organic layer is separated, and the aqueous layer is extracted with ether. The combined organic layers are washed with satd aq Na2S2O3 and brine, dried (MgSO4), filtered, and concentrated. Purification by flash column chromatography on SiO2 (hexanes/ethyl acetate, 10:1) affords the alcohol as a clear oil.
Workup
- additionAfter the addition
- stirringthe resulting turbid mixture is stirred at 25° C. for 8 hours
- customThe organic layer is separated
- extractionthe aqueous layer is extracted with ether
- washThe combined organic layers are washed with satd aq Na2S2O3 and brine
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
- customPurification by flash column chromatography on SiO2 (hexanes/ethyl acetate, 10:1)
Sources & evidence
- ORD record
- ord-99735aca8c734e0ab4507908ef4eafed
- Source dataset
- uspto-grants-2002_12
- Patent number
- US06489314B1
Reaction notes
Loading…