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Hydrochloric Acid → HCID 21619378, compound

HRID 605594
Notes
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Reaction equation

HRID 605594 reaction equation
[Si:1]([O:18][CH:19]1[CH2:24][CH2:23][CH:22]([C:25]([O:27]CC)=[O:26])[CH2:21][CH2:20]1)([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.[OH-].[Na+].Cl>CO.O1CCCC1>[Si:1]([O:18][CH:19]1[CH2:20][CH2:21][CH:22]([C:25]([OH:27])=[O:26])[CH2:23][CH2:24]1)([C:14]([CH3:17])([CH3:15])[CH3:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58018637HCID 58018637, compound

Product 1

HCID 21619378HCID 21619378, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 64.2 g of ethyl 4-((tert-butyl(diphenyl)silyl)oxy)cyclohexanecarboxylate in 200 ml of methanol and 200 ml of tetrahydrofuran was added 58 ml of 5 M aqueous sodium hydroxide solution, followed by stirring at room temperature overnight. The reaction mixture was neutralized with 5 M aqueous hydrochloride solution, followed by removal of the methanol and tetrahydrofuran in vacuo, and the resulting residue was extracted with ethyl acetate. The obtained ethyl acetate solution was washed with brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated in vacuo to give the title compound.

Workup

  1. customfollowed by removal of the methanol and tetrahydrofuran in vacuo
  2. extractionthe resulting residue was extracted with ethyl acetate
  3. washThe obtained ethyl acetate solution was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-9fbcc9cddb5e4511a7ca590798112841
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07915263B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes