Chlorotrimethylsilane → HCID 59557685, compound

HRID 1175330Notes

Reaction equation

HRID 1175330 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH3:16])=[CH:11][CH:10]=2)[C:5]([Cl:17])=[CH:4][C:3]=1[CH2:18][O:19][CH2:20][CH2:21][C:22]#[CH:23].[Li+].CC([N-]C(C)C)C.[Si:32](Cl)([CH3:35])([CH3:34])[CH3:33]>O>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([CH2:15][CH3:16])=[CH:13][CH:14]=2)[C:5]([Cl:17])=[CH:4][C:3]=1[CH2:18][O:19][CH2:20][CH2:21][C:22]#[C:23][Si:32]([CH3:35])([CH3:34])[CH3:33]

Participants

5

Reactant 3

HCID 6397Chlorotrimethylsilane2×HCID 2724682Lithium diisopropylamideHCID 59557720HCID 59557720, compound

Product 1

HCID 59557685HCID 59557685, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a cooled solution (−78° C.) of 1-bromo-2-((but-3-ynyloxy)methyl)-4-chloro-5-(4-ethylbenzyl)benzene (BT) (96 mg, 0.245 mmol) was added LDA (2M in THF, 0.18 mL, 0.36 mmol). After stirring for 20 min, TMS-Cl (50 μL, 0.393 mmol) was added. After stirring for another 2.5 h, additional TMS-Cl (30 μL, 0.236 mmol) was added. The reaction solution was stirred at −78° C. for 70 min and then warmed to room temperature with stirring for 1.5 h. Water was added and the mixture was extracted with ethyl acetate and the extracts were washed with brine, and dried over Na2SO4. The solution was concentrated and the resulting residue was purified by preparative TLC to afford 72 mg of title product.

Workup

  1. stirringAfter stirring for another 2.5 h
  2. stirringThe reaction solution was stirred at −78° C. for 70 min
  3. stirringwith stirring for 1.5 h
  4. extractionthe mixture was extracted with ethyl acetate
  5. washthe extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationThe solution was concentrated
  8. customthe resulting residue was purified by preparative TLC

Sources & evidence

ORD record
ord-3de362baf4cb41a3a675bfe71a959578
Source dataset
uspto-grants-2010_11
Patent number
US07838498B2

Reaction notes

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