Ammonium Chloride → HCID 18433588, compound

HRID 2306271Notes

Reaction equation

HRID 2306271 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:19][Si](C(C)C)(C(C)C)C(C)C)[CH:17]=2)[CH:12]=[CH:11][C:10]=1[Si:30]([CH3:33])([CH3:32])[CH3:31])=[O:7])([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-].[NH4+].[Cl-]>C1COCC1>[C:1]([O:5][C:6]([NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([OH:19])[CH:17]=2)[CH:12]=[CH:11][C:10]=1[Si:30]([CH3:33])([CH3:31])[CH3:32])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 18433505HCID 18433505, compound

Product 1

HCID 18433588HCID 18433588, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 1-(tert-butoxycarbonylamino)-7-(triisopropylsilyloxy)-2-(trimethylsilyl)naphthalene, as described above in Step B, (9.72 g, 19.9 mmol) in THF (200 mL) at 0° C. was added TBAF (1.0 M in THF, 20.9 mL, 20.9 mmol). The resulting mixture was stirred at 0° C. for 15 min then poured into dilute aqueous NH4Cl (250 mL) and extracted with CH2Cl2 (500 mL). The organic extract was dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by flash column chromatography on silica, eluting with CH2Cl2—10% EtOAc to yield the desired product.

Workup

  1. extractionextracted with CH2Cl2 (500 mL)
  2. extractionThe organic extract
  3. dry with materialwas dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash column chromatography on silica
  7. washeluting with CH2Cl2—10% EtOAc

Sources & evidence

ORD record
ord-ea8bb8e6d40943bf8645558d42888b91
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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