Ammonium Chloride → HCID 15986324, compound

HRID 33957Notes

Reaction equation

HRID 33957 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-83a02c6be6f546ae8a13f2c39b9c037a
Source dataset
uspto-grants-2008_09
Patent number
US07429681B2

Reaction notes

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