Ammonium Chloride → HCID 15986324, compound

HRID 1944644Notes

Reaction equation

HRID 1944644 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]([C:13]([C:15]2[C:21]3[CH:22]=[C:23]([O:30][CH3:31])[C:24]([O:28][CH3:29])=[C:25]([O:26][CH3:27])[C:20]=3[CH2:19][CH2:18][CH2:17][CH:16]=2)=[O:14])[CH:8]=[CH:9][C:10]=1[O:11][CH3:12])(C)C.[Al+3].[Cl-].[Cl-].[Cl-].[NH4+].[Cl-]>C(Cl)Cl>[OH:4][C:5]1[CH:6]=[C:7]([C:13]([C:15]2[C:21]3[CH:22]=[C:23]([O:30][CH3:31])[C:24]([O:28][CH3:29])=[C:25]([O:26][CH3:27])[C:20]=3[CH2:19][CH2:18][CH2:17][CH:16]=2)=[O:14])[CH:8]=[CH:9][C:10]=1[O:11][CH3:12]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 6451240Aluminum(III) ChlorideHCID 68923389(3-Isopropoxy-4-methoxy-phenyl)-(1,2,3-trimethoxy-8,9-dihydro-7H-benzocyclohepten-5-yl)-methanone

Product 1

HCID 15986324HCID 15986324, compoundYield 56.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

97 (0.07 g, 0.16 mmol) was dissolved in 10 mL of anhydrous CH2Cl2 under nitrogen at 0° C. Anhydrous AlCl3 (44 mg, 0.33 mmol) was added and the reaction mixture was stirred for 2 h at 0° C. Saturated NH4Cl (5 mL) was added and the organic phase was separated. The aqueous layer was extracted with CH2Cl2 (10 mL) and the combined organic phases were dried over Na2SO4, filtered, solvents evaporated under reduced pressure. The crude product was purified by column chromatography (30:70 EtOAc:Hexanes) to yield tan colored oil as product 24 (35 mg, 56% yield). Rf: 0.23 (60:40 Hex:EA).

Workup

  1. customthe organic phase was separated
  2. extractionThe aqueous layer was extracted with CH2Cl2 (10 mL)
  3. dry with materialthe combined organic phases were dried over Na2SO4
  4. filtrationfiltered
  5. customsolvents evaporated under reduced pressure
  6. customThe crude product was purified by column chromatography (30:70 EtOAc:Hexanes)

Sources & evidence

ORD record
ord-d03624852d304c138678b600d67cb42b
Source dataset
uspto-grants-2013_03
Patent number
US08394859B2

Reaction notes

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