Isopropanol → HCID 53653153, compound

HRID 260298Notes

Reaction equation

HRID 260298 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:9]1([CH:15]=[C:16]2[NH:25][CH:24]3[CH2:26][CH:19]4[CH:20]([CH2:21][CH2:22][CH2:23]3)[CH:18]4[C:17]2=[O:27])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(O)(C)C>CCOCC.C1(C)C=CC=CC=1>[C:1]1([CH:15]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:16]2[NH:25][CH:24]3[CH2:26][CH:19]4[CH:20]([CH2:21][CH2:22][CH2:23]3)[CH:18]4[C:17]2=[O:27])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 70143786HCID 70143786, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 53653153HCID 53653153, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a 100 mL three-neck round-bottomed flask equipped with a condenser and nitrogen inlet was added 0.71 mL (4.21 mmol) of a 3M solution of phenyl magnesium bromide in ether. The solution was cooled to 0° C. and a solution of 818 mg (3.24 mmol) 9-phenylmethylene-10-azatricyclo[4.4.1.05,7 ]undecan-8-one in 16 mL toluene was added. The reaction was warmed to room temperature, stirred for 2 hours, and then quenched with aqueous ammonium chloride solution. The reaction was extracted with ethyl acetate, and the organic layer was dried over sodium sulfate and evaporated. The residue was chromatographed on silica gel using hexane/ethyl acetate as eluent to afford an oil, 196 mg (18%). This material gave a solid from isopropanol, mp 178-181° C.

Workup

  1. customTo a 100 mL three-neck round-bottomed flask equipped with a condenser and nitrogen inlet
  2. temperatureThe reaction was warmed to room temperature
  3. customquenched with aqueous ammonium chloride solution
  4. extractionThe reaction was extracted with ethyl acetate
  5. dry with materialthe organic layer was dried over sodium sulfate
  6. customevaporated
  7. customThe residue was chromatographed on silica gel
  8. customto afford an oil, 196 mg (18%)

Sources & evidence

ORD record
ord-256ca58ab3c0436abd45234f53c38d53
Source dataset
uspto-grants-1996_06
Patent number
US05527808

Reaction notes

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