Ammonium Chloride → HCID 15047376, compound

HRID 1162956Notes

Reaction equation

HRID 1162956 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].C([Si](C)(C)[O:24][CH2:25][CH2:26][O:27][CH:28]1[CH2:33][O:32][CH:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:30][CH2:29]1)(C)(C)C.[Cl-].[NH4+]>C1COCC1>[C:34]1([CH:31]2[O:32][CH2:33][CH:28]([O:27][CH2:26][CH2:25][OH:24])[CH2:29][O:30]2)[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 57558159HCID 57558159, compound

Product 1

HCID 15047376HCID 15047376, compoundYield 17.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of TBAF in 1 M-THF (1 mL, 1.00 mmol) was added to 5 mL of a solution of crude tert-butyldimethyl-[2-(2-phenyl-[1,3]dioxan-5-yloxy)ethoxy]silane (343 mg, 1.01 mmol) obtained in Step A in THF, and the mixture was stirred at room temperature for 16 hours. Aqueous saturated ammonium chloride was added to the mixture, followed by extraction with ethyl acetate. The extract was washed with saturated saline and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (methylene chloride:methanol=50:1) to obtain 2-(2-phenyl-[1,3]dioxan-5-yloxy)ethanol (39 mg, yield: 17%) as a colorless oil.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe extract was washed with saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (methylene chloride:methanol=50:1)

Sources & evidence

ORD record
ord-682eea5c08e541d9b6e0e51bcdcb4713
Source dataset
uspto-grants-2010_10
Patent number
US07820693B2

Reaction notes

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