2-[3,4-Bis(tert-butyldimethylsilanyloxy-methyl)phenoxymethyl]-5-((e)-4,4-dibromo-1-ethylbuta-1,3-dienyl)thiophene → 2-[3,4-bis(tert-butyldimethylsilanyloxymethyl)phenoxymethyl]-5-((E)-1-ethyl-but-1-en-3-ynyl)thiophene
Reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:28]=[CH:29][C:30]=1[CH2:31][O:32][Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34])[O:13][CH2:14][C:15]1[S:16][C:17](/[C:20](/[CH2:26][CH3:27])=[CH:21]/[CH:22]=[C:23](Br)Br)=[CH:18][CH:19]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([Li])CCC>C1COCC1>[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:28]=[CH:29][C:30]=1[CH2:31][O:32][Si:33]([C:36]([CH3:37])([CH3:39])[CH3:38])([CH3:34])[CH3:35])[O:13][CH2:14][C:15]1[S:16][C:17](/[C:20](/[CH2:26][CH3:27])=[CH:21]/[C:22]#[CH:23])=[CH:18][CH:19]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
3.9 g (5.4 mmol) of 2-[3,4-bis(tert-butyldimethylsilanyloxymethyl)phenoxymethyl]-5-((E)-4,4-dibromo-1-ethylbuta-1,3-dienyl)thiophene are dissolved in 100 mL of THF and the mixture is cooled to −78° C. 4.4 mL (11 mmol) of 2.5 M butyllithium are added slowly and the reaction medium is stirred at the same temperature for 1 hour. After the usual treatment and chromatography on silica gel (eluent: 96 heptane/4 ethyl acetate), the desired product is obtained in the form of a brown oil.
Sources & evidence
- ORD record
- ord-ff3cda8be36949c5a4bede53a3320da3
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06706725B1
Reaction notes
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