Tetrahydrofuran → HCID 67061947, compound

HRID 337592Notes

Reaction equation

HRID 337592 reaction equation
C1COCC1.[Cl:6][C:7]1[CH:8]=[C:9]([CH2:23][CH2:24][NH:25][C:26](=[O:29])[CH2:27][CH3:28])[CH:10]=[C:11]([CH2:14][O:15][Si](C(C)(C)C)(C)C)[C:12]=1[Cl:13].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>CCOCC>[Cl:6][C:7]1[CH:8]=[C:9]([CH2:23][CH2:24][NH:25][C:26](=[O:29])[CH2:27][CH3:28])[CH:10]=[C:11]([CH2:14][OH:15])[C:12]=1[Cl:13]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 66896471HCID 66896471, compound

Product 1

HCID 67061947HCID 67061947, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a THF (0.12 M) solution of N-{2-[3,4-dichloro-5-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)phenyl]ethyl}propanamide (1 eq.) from the previous step was added TBAF (1.0 M THF solution, 1.1 eq.). The resulting solution was stirred at RT for 2 h. The now orange solution was diluted with ether and quenched with 1 N aq. NaOH. The aqueous layer was separated and back-extracted with ether. The combined organic extracts were washed further with water and brine, dried over Na2SO4 and filtered. Concentration of the filtrate in vacuo afforded the crude title compound as a pale yellow oil.

Workup

  1. customquenched with 1 N aq. NaOH
  2. customThe aqueous layer was separated
  3. extractionback-extracted with ether
  4. washThe combined organic extracts were washed further with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered

Sources & evidence

ORD record
ord-c78c8596dc364e12ba6725682f741d70
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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