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Ammonium Chloride → 1-({[tert-Butyl(diphenyl)silyl]oxy}methyl)cyclopropan-1-ol

HRID 1820610
Notes
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Reaction equation

HRID 1820610 reaction equation
[Si:1]([O:18][CH2:19][C:20]([O:22]CC)=O)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:25]([Mg]Br)[CH3:26].[Cl-].[NH4+]>O1CCCC1.CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4]>[Si:1]([O:18][CH2:19][C:20]1([OH:22])[CH2:26][CH2:25]1)([C:14]([CH3:15])([CH3:17])[CH3:16])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 59464758(tert-Butyl-diphenyl-silanyloxy)-acetic acid ethyl esterHCID 178418443HCID 178418443, compound

Product 1

HCID 529878051-({[tert-Butyl(diphenyl)silyl]oxy}methyl)cyclopropan-1-olYield 100%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxide
Catalyst
HCID 8028TetrahydrofuranSolvent2×

Procedure

According to the description in a reference (see: Syn. Lett. 07, 1053-1054, 1999), the title compound was prepared as follows. 12 g (35 mmole) of ethyl 2-{[t-butyl(diphenyl)silyl]oxy}acetate was dissolved in 200 ml of tetrahydrofuran (THF) and 2.2 ml of titaniumtetraisopropoxide was added thereto. To the mixture was slowly added 29.2 ml of ethylmagnesiumbromide (3.0M in THF), and the reaction solution was stirred for 12 hours at room temperature. 20 ml of saturated ammonium chloride was added to stop the reaction. About 150 ml of tetrahydrofuran (THF) used as a solvent was removed by distillation under reduced pressure, and the reaction mixture was extracted twice with 200 ml of ethyl acetate. The ethyl acetate extract was distilled under reduced pressure to give 11.4 g (Yield 100%) of the title compound as a white solid.

Workup

  1. customthe title compound was prepared
  2. customthe reaction
  3. customwas removed by distillation under reduced pressure
  4. extractionthe reaction mixture was extracted twice with 200 ml of ethyl acetate
  5. extractionThe ethyl acetate extract
  6. distillationwas distilled under reduced pressure

Sources & evidence

ORD record
ord-45e0c26fb45541f0b3e3c1bbed432384
Source dataset
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07605147B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes