Water → [(e)-5-(5-Bromo-2-thienyl)-1,1-diethylhex-4-enyloxy]triethylsilane

HRID 49320

Reaction equation

[Br:1][C:2]1[S:6][C:5](/[C:7](/[CH3:17])=[CH:8]/[CH2:9][CH2:10][C:11]([CH2:15][CH3:16])([OH:14])[CH2:12][CH3:13])=[CH:4][CH:3]=1.C(N(CC)CC)C.FC(F)(F)S(O[Si:31]([CH2:36][CH3:37])([CH2:34][CH3:35])[CH2:32][CH3:33])(=O)=O.O>ClCCl.CN(C)C1C=CN=CC=1>[Br:1][C:2]1[S:6][C:5](/[C:7](/[CH3:17])=[CH:8]/[CH2:9][CH2:10][C:11]([CH2:15][CH3:16])([CH2:12][CH3:13])[O:14][Si:31]([CH2:36][CH3:37])([CH2:34][CH3:35])[CH2:32][CH3:33])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2.2 g (6.9 mmol) of (E)-7-(5-bromo-2-thienyl)-3-ethyloct-6-en-3-ol are dissolved in 50 mL of dichloromethane. 25 mg (0.2 mmol) of 4-dimethylaminopyridine and 4.8 mL of triethylamine (34.8 mmol) are added and the reaction medium is cooled to 0° C. 3.9 mL (17.4 mmol) of triethylsilyl trifluoromethanesulphonate are added dropwise. After the addition, the reaction medium is warmed to room temperature and then treated with water and extracted with dichloromethane. After separation of the phases by settling, drying and concentration of the organic phases under reduced pressure, the residue obtained is purified by chromatography on a column of silica. A yellow oil is obtained (m=2.3 g; Y=97%).

Workup

additionAfter the addition
customthe reaction
temperaturemedium is warmed to room temperature
extractionextracted with dichloromethane
customAfter separation of the phases
customdrying
customconcentration of the organic phases under reduced pressure, the residue obtained
customis purified by chromatography on a column of silica
customA yellow oil is obtained (m=2.3 g; Y=97%)

Sources & evidence

ORD record: ord-7f853feec8ee49778e0a9d7dd13d66e6
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06706725B1

Linked notes

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