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Ammonium Chloride → 2-[1-(2-tert-Butyldiphenylsiloxyethyl)cyclohexyl]ethanol

HRID 1820311
Notes
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Reaction equation

HRID 1820311 reaction equation
[C:1]([Si:5](Cl)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2].[OH:19][CH2:20][CH2:21][C:22]1([CH2:28][CH2:29][OH:30])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.[Cl-].[NH4+]>C(Cl)Cl>[O:19]([CH2:20][CH2:21][C:22]1([CH2:28][CH2:29][OH:30])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1)[Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 76657Cyclohexane-1,1-diethanolHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 574278602-[1-(2-tert-Butyldiphenylsiloxyethyl)cyclohexyl]ethanolYield 71.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butylchlorodiphenylsilane (34.4 mL, 0.132 mol) was added dropwise to a solution of 2-[1-(2-hydroxyethyl)cyclohexyl]ethanol (21.7 g, 0.126 mol) in methylene chloride (280 mL) while cooling on ice. After stirring the mixture for 14 hours at room temperature, 25% aqueous ammonium chloride (300 mL) was added and extraction was performed. The organic layer was washed with saturated aqueous sodium chloride, and then the organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (500 g Merck Art. 9385, hexane:ethyl acetate=4:1) to obtain the title compound as a colorless oil (36.8 g) (2 steps, 60% yield).

Workup

  1. temperaturewhile cooling on ice
  2. extractionextraction
  3. washThe organic layer was washed with saturated aqueous sodium chloride
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (500 g Merck Art. 9385, hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-866f6fd61ab44a628b1f78afe9d2aef4
Source dataset
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07601843B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes