Tetraethylene Glycol → 13,13,14,14-Tetramethyl-3,6,9,12-tetraoxa-13-silapentadecan-1-ol

HRID 1157070Notes

Reaction equation

HRID 1157070 reaction equation
[CH2:1]([OH:13])[CH2:2][O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][OH:12].[CH3:14][C:15]([Si:18](Cl)([CH3:20])[CH3:19])([CH3:17])[CH3:16].C(N(CC)CC)C>ClCCl>[C:15]([Si:18]([CH3:20])([CH3:19])[O:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][O:6][CH2:5][CH2:4][O:3][CH2:2][CH2:1][OH:13])([CH3:17])([CH3:16])[CH3:14]

Participants

5

Reactant 3

HCID 8200Tetraethylene GlycolHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 1482766913,13,14,14-Tetramethyl-3,6,9,12-tetraoxa-13-silapentadecan-1-olYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tetraethylene glycol, 4c (1.12 g, 5.77 mmol) and TBDMSCl (0.87 g, 5.77 mmol) were dissolved in dichloromethane (25 ml) followed by triethyl amine (1.46 g, 14.4 mmol). The solution was stirred at room temperature for 2 hours. After standard workup with dichloromethane, the residue was purified by silica gel column chromatography (50% ethyl acetate in hexane) to afford 5c (744 mg, 42%): 1H NMR δ 3.66 (m, 16H), 2.51 (t, 1H, J=5.86 Hz), 0.89 (s, 9H), 0.07 (s, 6H).

Workup

  1. customAfter standard workup with dichloromethane, the residue was purified by silica gel column chromatography (50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-bc1182f303b44d2eb06e98753e7b1824
Source dataset
uspto-grants-2010_10
Patent number
US07807135B2

Reaction notes

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