2-Bromothiophene → HCID 66609090, compound
Reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][CH:6]=1.[Li]CCCC.[CH3:12][CH2:13][CH2:14][C:15](=[O:19])[CH2:16][CH2:17][CH3:18]>C1COCC1>[S:3]1[CH:4]=[CH:5][CH:6]=[C:2]1[C:15]([OH:19])([CH2:16][CH2:17][CH3:18])[CH2:14][CH2:13][CH3:12]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
A solution of 2-bromothiophene (10.0 g, 61.5 mmol) in dry THF (60 mL) was cooled to −78° C. under nitrogen. A solution of n-BuLi (2.5 M, 27.0 mL, 67.5 mmol) was then added slowly, and the resulting mixture was stirred at −78° C. for 2 hours, before a solution of 4-heptanone (8.5 g, 74.4 mmol) in dry THF (10 mL) was added slowly. This mixture was stirred at −78° C. for an additional 1 hour, and then allowed to warm to room temperature, and stirred at room temperature overnight. Most of the solvent was removed in vacuo, and the residue was subjected to flash column chromatography on silica gel with a hexane:EtOAc (3:1, v/v) mixture, leading to a colorless oil as the product (10.2 g, 83.5%).
Workup
- additionwas added slowly
- temperatureto warm to room temperature
- stirringstirred at room temperature overnight
- customMost of the solvent was removed in vacuo
Sources & evidence
- ORD record
- ord-9640c1b4ed984adfb4657f475a4649ef
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08598575B2
Reaction notes
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