Water → HCID 23130648, compound

HRID 2080075Notes

Reaction equation

HRID 2080075 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:25]=[CH:24][C:21]([CH2:22]Br)=[CH:20][CH:19]=1.O>O1CCCC1.C(OCC)(=O)C>[F:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][C:7]2[S:11][C:10]([CH:12]3[O:16][CH2:15][CH2:14][O:13]3)=[CH:9][CH:8]=2)=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 962WaterHCID 680214-Fluorobenzyl bromideHCID 122699702-(5-Bromothiophen-2-Yl)-1,3-DioxolaneHCID 178418339Butyllithium

Product 1

HCID 23130648HCID 23130648, compoundYield 26.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

n-Butyl lithium (2.6N hexane solution, 3.3 mL, 8.47 mmol) was added dropwise to a solution of 2-(5-bromo-thiophen-2-yl)-[1,3]dioxolane (1.8 g, 7.7 mmol) in tetrahydrofuran (20 mL) that had been cooled to from −75° to −70° C., and the solution was stirred for 30 minutes. 4-Fluorobenzyl bromide (1.1 mL, 8.47 mmol) was added dropwise to this reaction solution while keeping it at −70° C. or less. After completion of dropwise addition, the reaction solution was gradually allowed to room temperature. Water and ethyl acetate were added to the reaction solution, which was then partitioned, silica gel was added to the organic layer, which was then evaporated in vacuo for adsorption, purification by silica gel column chromatography (hexane, then hexane:ethyl acetate=20:1, then 10:1) was carried out, and the title compound (560 mg, 2.04 mmol, 26.4%) was obtained as a brown oil.

Workup

  1. temperaturehad been cooled to from −75° to −70° C.
  2. customat −70° C. or less
  3. additionAfter completion of dropwise addition
  4. customwas gradually allowed to room temperature
  5. customwas then partitioned
  6. additionsilica gel was added to the organic layer, which
  7. customwas then evaporated in vacuo for adsorption, purification by silica gel column chromatography (hexane

Sources & evidence

ORD record
ord-5463312390224c768248c6fb2b25e174
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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