Trimethylamine → [(15-Bromopentadecyl)oxy](tert-butyl)dimethylsilane

HRID 1768449Notes

Reaction equation

HRID 1768449 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][OH:17].CN(C)C.[Si:22](Cl)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23].CN(C1C=CC=CN=1)C.[Cl-].[NH4+]>C(Cl)Cl>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]

Participants

7

Reactant 5

HCID 1146TrimethylamineHCID 218852-DimethylaminopyridineHCID 25517Ammonium ChlorideHCID 28928tert-Butyldimethylsilyl chlorideHCID 54385015-Bromopentadecan-1-ol

Product 1

HCID 23615174[(15-Bromopentadecyl)oxy](tert-butyl)dimethylsilaneYield 94.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

15-Bromo-pentadecan-1-ol (2.3 g, 7.49 mmol) dissolved in methylene chloride (23 mL) was mixed with trimethylamine (2.1 mL, 14.98 mmol), t-butyldimethylsilyl chloride (2.03 g, 13.48 mmol), and dimethylaminopyridine (457.6 mg, 3.74 mmol). The mixture was stirred for one hour at room temperature. Subsequently, aqueous saturated ammonium chloride solution was added to the reaction mixture for separation into a methylene chloride layer (200 mL) and an aqueous layer (200 mL). The organic layer was dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by means of silica gel column flash chromatography (hexane/ethyl acetate=99/1), to thereby afford 2.98 g (7.07 mmol) of 15-bromo-1-(t-butyldimethylsiloxy)pentadecane.

Workup

  1. dry with materialThe organic layer was dried over magnesium sulfate
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified by means of silica gel column flash chromatography (hexane/ethyl acetate=99/1)

Sources & evidence

ORD record
ord-878b5950446146fa8720cc053302e1db
Source dataset
uspto-grants-2007_06
Patent number
US07235700B2

Reaction notes

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