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Ethanol → 1-(3-(Di(tert-butyldimethylsiloxy)-methyl-silanyl)-propoxy)-3-(2-(2-(2-hydroxy-ethoxy)-ethoxy)-ethylamino)-propan-2-ol

HRID 2384127
Notes
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Reaction equation

HRID 2384127 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][OH:10].[C:11]([Si:15]([CH3:35])([CH3:34])[O:16][Si:17]([CH:27]([CH2:30][CH:31]1[CH2:33][O:32]1)CC)([CH3:26])[O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])([CH3:14])([CH3:13])[CH3:12].[CH2:36]([OH:38])[CH3:37]>>[O:18]([Si:17]([O:16][Si:15]([C:11]([CH3:12])([CH3:14])[CH3:13])([CH3:35])[CH3:34])([CH3:26])[CH2:27][CH2:30][CH2:31][O:32][CH2:33][CH:36]([OH:38])[CH2:37][NH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][OH:10])[Si:19]([C:22]([CH3:25])([CH3:23])[CH3:24])([CH3:20])[CH3:21]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 3

HCID 702Ethanol2×HCID 95875Ethanol, 2-[2-(2-aminoethoxy)ethoxy]-HCID 866322801,5-Di(tert-butyl)-3-(oxiranylmethylpropyl)-1,1,3,5,5-Pentamethyltrisiloxane

Product 1

HCID 577725651-(3-(Di(tert-butyldimethylsiloxy)-methyl-silanyl)-propoxy)-3-(2-(2-(2-hydroxy-ethoxy)-ethoxy)-ethylamino)-propan-2-ol

Conditions

Temperature
70 °C

Procedure

2-(2-(2-Amino-ethoxy)-ethoxy)-ethanol (3.52 g) and ethanol (40 mL) were charged to a 100 mL RB flask equipped with a magnetic stirrer. The mixture was stirred and heated to 70° C. 1,5-Di(tert-butyl)-3-(oxiranylmethylpropyl)-1,1,3,5,5-Pentamethyltrisiloxane (2.0 g) mixed with ethanol (10 mL) was placed in an addition funnel and added dropwise to the flask. The mixture was stirred and maintained at 70° C. for an additional 4 hours. Reaction progress was monitored by NMR spectroscopy. Upon reaction completion, the ethanol was removed by rotary evaporation, and the mixture was distilled under vacuum to remove impurities and excess raw material.

Workup

  1. customequipped with a magnetic stirrer
  2. customwas placed in an addition funnel
  3. additionadded dropwise to the flask
  4. stirringThe mixture was stirred
  5. temperaturemaintained at 70° C. for an additional 4 hours
  6. customReaction progress
  7. customUpon reaction completion
  8. customthe ethanol was removed by rotary evaporation
  9. distillationthe mixture was distilled under vacuum
  10. customto remove impurities and excess raw material

Sources & evidence

ORD record
ord-ff48101487e64bd9b0a3a23eb983b805
Source dataset
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08263669B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes