Ammonium Chloride → HCID 21102307, compound

HRID 1353149Notes

Reaction equation

HRID 1353149 reaction equation
[CH3:1][C:2]([CH3:5])([O-])C.[K+].[CH3:7][O:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][CH2:13][C:14]2=O.[Cl-].[NH4+]>O1CCCC1>[C:5]1(=[C:14]2[C:15]3[C:10](=[C:9]([O:8][CH3:7])[CH:18]=[CH:17][CH:16]=3)[CH2:11][CH2:12][CH2:13]2)[CH2:2][CH2:1]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 366205-MethoxytetraloneHCID 23665647Potassium tert-butoxide

Product 1

HCID 21102307HCID 21102307, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under ice-cooling, to an anhydrous tetrahydrofuran (200 ml) solution of (3-bromopropyl)triphenylphosphinium bromide (19.8 g), potassium t-butoxide (9.58 g) was added, followed by stirring at room temperature for 1.5 hours. To the reaction mixture, 5-methoxy-1-tetralone (5.0 g) was added, followed by stirring at room temperature for 5 hours. The reaction mixture was poured into a saturated aqueous ammonium chloride solution. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with saturated saline, dried with anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to thereby obtain the title compound (5.66 g) having the following physical data.

Workup

  1. additionwas added
  2. stirringby stirring at room temperature for 5 hours
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layer was washed with saturated saline
  5. dry with materialdried with anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-38997bae1d004b689736b6d6731b6481
Source dataset
uspto-grants-2007_05
Patent number
US07220864B2

Reaction notes

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