Ethyl Acetate → HCID 178430167, compound

HRID 1864688Notes

Reaction equation

HRID 1864688 reaction equation
[O:1]([C@@H:9]1[C@@H:16]2[N:12](/[C:13](=[N:17]/[C:18]3[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[C:20]([Cl:26])[C:19]=3[CH3:27])/[O:14][CH2:15]2)[CH2:11][CH2:10]1)[Si](C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].[NH4+].[Cl-].CCOC(C)=O>C1COCC1>[OH:1][C@@H:9]1[C@@H:16]2[N:12](/[C:13](=[N:17]/[C:18]3[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[C:20]([Cl:26])[C:19]=3[CH3:27])/[O:14][CH2:15]2)[CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 178430170HCID 178430170, compound

Product 1

HCID 178430167HCID 178430167, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of compound 2D (11.0 mg, 0.0250 mmol) in THF (1 mL) at 0° C. was added a 1.0 M TBAF solution in THF (0.250 mL, 0.250 mmol). After stirring at rt for 1 h, saturated aqueous NH4Cl and EtOAc were added. The layers were separated, and the organic layer was washed with brine, then dried over MgSO4, filtered and concentrated. Purification via flash chromatography (silica gel, 0-85% EtOAc in hexane) provided the title compound (4.6 mg). LCMS: m/z 292 [M+H]+.

Workup

  1. customThe layers were separated
  2. washthe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification via flash chromatography (silica gel, 0-85% EtOAc in hexane)

Sources & evidence

ORD record
ord-9da51211d12a441f91dde74f1ceaaa2b
Source dataset
uspto-grants-2009_12
Patent number
US07625923B2

Reaction notes

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