Chlorotrimethylsilane → 403613-26-3

HRID 548244Notes

Reaction equation

HRID 548244 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:17][Si:18]([CH3:21])([CH3:20])Cl>C1COCC1>[CH3:17][Si:18]([CH3:21])([CH3:20])[O:7][CH2:6][C:5]1[CH:8]=[CH:9][C:2]([NH2:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 693314-Aminobenzyl alcohol

Product 1

HCID 11401321403613-26-3Yield 945.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-amino benzyl alcohol (16.0 g, 13.0 mmol, 1.0 eq) in THF (400 mL), was added triethylamine (18.9 mL, 13.6 mmol, 1.05 eq) followed by trimethylchlorosilane (17.2 mL, 13.6 mmol, 1.05 eq). The reaction mixture was stirred under a nitrogen atmosphere overnight at room temperature. THF was evaporated under vacuum and the mixture partitioned with ethyl acetate (300 mL) and water (300 mL). The organic phase was isolated and the aqueous layer re-extracted with ethyl acetate (2×100 mL). The combined organic phases were washed with brine (2×150 mL), dried (MgSO4), filtered and concentrated in vacuo. The product was obtained as a yellow oil (24.0 g, 95% yield) and used in stage 4 without further purification.

Workup

  1. customTHF was evaporated under vacuum
  2. customthe mixture partitioned with ethyl acetate (300 mL) and water (300 mL)
  3. customThe organic phase was isolated
  4. extractionthe aqueous layer re-extracted with ethyl acetate (2×100 mL)
  5. washThe combined organic phases were washed with brine (2×150 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-646a523bf0ae4ef7b0614c85887ec9b7
Source dataset
uspto-grants-2011_05
Patent number
US07939666B2

Reaction notes

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