Water → HCID 23130519, compound

HRID 2080084Notes

Reaction equation

HRID 2080084 reaction equation
C([Li])CCC.Br[C:7]1[S:11][C:10]([CH:12]2[O:16][CH2:15][CH2:14][O:13]2)=[CH:9][CH:8]=1.[F:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH2:21]Br.O>O1CCCC1.C(OCC)(=O)C>[F:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH2:21][C:7]1[S:11][C:10]([CH:12]2[O:16][CH2:15][CH2:14][O:13]2)=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 680073-Fluorobenzyl bromideHCID 122699702-(5-Bromothiophen-2-Yl)-1,3-DioxolaneHCID 178418339Butyllithium

Product 1

HCID 23130519HCID 23130519, compoundYield 13.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

n-Butyl lithium (2.44N hexane solution, 6.4 mL, 16.9 mmol) was added dropwise to a solution of 2-(5-bromo-thiophen-2-yl)-[1,3]dioxolane (3.0 g, 13 mmol) in tetrahydrofuran (30 mL) at from −75° C. to −69° C., and the solution was stirred for 17 minutes. 3-Fluorobenzyl bromide (1.7 mL, 14.3 mmol) was added dropwise to this reaction solution at from −75° C. to −69° C. After dropwise addition was completed, the reaction solution was gradually allowed to room temperature. Water and ethyl acetate were added to the reaction solution, which was then partitioned, the organic layer was concentrated in vacuo, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1), and the title compound (478 mg, 1.81 mmol, 13.9%) was obtained as a brown oil.

Workup

  1. additionAfter dropwise addition
  2. customwas gradually allowed to room temperature
  3. customwas then partitioned
  4. concentrationthe organic layer was concentrated in vacuo
  5. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-1fdcdf4dac4c4950b384511c2549b24e
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

Loading…