Triethylamine → 4-(4-((6-((tert-butyldimethylsilyl)oxy)hexyl)oxy)butyl)-N-methylaniline

HRID 1944884Notes

Reaction equation

HRID 1944884 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][OH:20])=[CH:5][CH:4]=1.[Si:21](Cl)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22].C(N(CC)CC)C>ClCCl.CN(C1C=CN=CC=1)C>[Si:21]([O:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][O:13][CH2:12][CH2:11][CH2:10][CH2:9][C:6]1[CH:5]=[CH:4][C:3]([NH:2][CH3:1])=[CH:8][CH:7]=1)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]

Participants

6

Reactant 3

HCID 8471Triethylamine2×HCID 28928tert-Butyldimethylsilyl chloride2×HCID 57516946HCID 57516946, compound

Product 1

HCID 585050534-(4-((6-((tert-butyldimethylsilyl)oxy)hexyl)oxy)butyl)-N-methylaniline

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of Intermediate 56 (0.92 g, 3.3 mmol) in dichloromethane was treated successively with tert-butyldimethylsilyl chloride (0.75 g, 5.0 mmol), DMAP (50 mg), and triethylamine (1.4 mL, 10 mmol). After a few minutes, additional quantities of tert-butyldimethylsilyl chloride (0.75 g, 5.0 mmol) and triethylamine (1 mL) were added. The mixture was filtered through a pad of Celite and concentrated. The residue was purified via automated flash silica gel chromatography, using a 40 g Silicycle SiliSep flash column (hexanes/ethyl acetate). Concentration of the desired fractions under reduced pressure provided the title compound as clear, colorless syrup (0.99 g, 76%). ES/MS calcd. for C23H44NO2Si+ 394.3. Found m/z=394.4 (M+H)+.

Workup

  1. waitAfter a few minutes
  2. filtrationThe mixture was filtered through a pad of Celite
  3. concentrationconcentrated
  4. customThe residue was purified via automated flash silica gel chromatography

Sources & evidence

ORD record
ord-ec8dde4e146b48c59d9f8eac06799d0f
Source dataset
uspto-grants-2013_03
Patent number
US08394829B2

Reaction notes

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