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

HRID 49320
Notes
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Reaction equation

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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 2733308Triethylsilyl trifluoromethanesulphonateHCID 17934786(e)-7-(5-Bromo-2-thienyl)-3-ethyloct-6-en-3-ol

Product 1

HCID 17934815[(e)-5-(5-Bromo-2-thienyl)-1,1-diethylhex-4-enyloxy]triethylsilane

Reagents, catalysts & solvents 2

HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 6344DichloromethaneSolvent

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

  1. additionAfter the addition
  2. customthe reaction
  3. temperaturemedium is warmed to room temperature
  4. extractionextracted with dichloromethane
  5. customAfter separation of the phases
  6. customdrying
  7. customconcentration of the organic phases under reduced pressure, the residue obtained
  8. customis purified by chromatography on a column of silica
  9. 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

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes