Reaction equation
[B:1](OC(C)C)([O:6]C(C)C)[O:2]C(C)C.Br[C:15]1[C:16]([CH:20]2[O:24]CCO2)=[CH:17][S:18][CH:19]=1.[Li]CCCC.Cl>C1(C)C=CC=CC=1.C1COCC1>[CH:20]([C:16]1[C:15]([B:1]([OH:6])[OH:2])=[CH:19][S:18][CH:17]=1)=[O:24]Participants
6
Conditions
- Temperature
- -78 °C
Procedure
To a 0.5M solution of B(Oi-Pr)3 (1.2 eq) in toluene/THF 4:1 was added a solution of 2-(4-bromo-3-thienyl)-1,3-dioxolane in toluene/THF 4:1, and the mixture was then cooled to −78° C. BuLi (1.5M in hexanes; 1.2 eq) was then added over 1 h, and the solution kept at this temperature for an additional h, then allowed to warm to −20° C. over 3 h; aq 1N HCl was added and the mixture stirred for an additional h at this temperature. Removal of volatiles gave an aqueous solution that was extracted with DCM; the combined organic phases were then washed with brine, dried over Na2SO4 and concentrated in vacuo. Yield: 95%.
Workup
- temperatureto warm to −20° C. over 3 h
- customRemoval of volatiles
- customgave an aqueous solution that
- extractionwas extracted with DCM
- washthe combined organic phases were then washed with brine
- dry with materialdried over Na2SO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-a0f53afc9c454528be29c1e7c46f6753
- Source dataset
- uspto-grants-2010_09
- Patent number
- US07795247B2
Linked notes
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