Ammonium Chloride → HCID 54141758, compound

HRID 249541Notes

Reaction equation

HRID 249541 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH3:19][C:20]([CH3:49])([CH2:33][S:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][Si](C(C)(C)C)(C)C)=[CH:37][CH:36]=1)[C:21]([O:23][CH2:24][O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:22].[Cl-].[NH4+]>C1COCC1>[CH3:19][C:20]([CH3:49])([CH2:33][S:34][C:35]1[CH:40]=[CH:39][C:38]([OH:41])=[CH:37][CH:36]=1)[C:21]([O:23][CH2:24][O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:22]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 54088927HCID 54088927, compound

Product 1

HCID 54141758HCID 54141758, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1.0M solution of tetra-n-butylammonium fluoride in THF (3.6 mL, 1.1 equiv) was added to the tert-butyldimethylsilylether (XXVII) (1.50 g, 3.3 mmol) in 25 mL of THF at -10° C. After 1 hour the reaction was acidified with saturated ammonium chloride (25 mL) and extracted with ether. The ether layer was washed with H2O, saturated NaCl, dried over anhydrous MgSO4 and concentrated. The residue was chromatographed on silica gel to give 0.92 g (82%) of V. 1H NMR (CDCl3) δ1.27 (s, 6H), 3.10 (s, 2H), 4.67 (s, 2H), 5.10 (br s, 1H), 5.28 (s, 2H), 6.74 (d, 2H, J=8.4 Hz), 7.2-7.4 (m, 7H); 13C NMR (CDCl3) δ25.10, 44.82, 47.19, 72.41, 89.38, 116.72, 128.07, 128.68, 128.76, 129.24, 134.49, 137.74, 155.91, 176.91.

Workup

  1. extractionextracted with ether
  2. washThe ether layer was washed with H2O, saturated NaCl
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel
  6. customto give 0.92 g (82%) of V

Sources & evidence

ORD record
ord-2095af05f0374abc80c064c8f6030533
Source dataset
uspto-grants-1993_05
Patent number
US05214191

Reaction notes

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