Carbon Tetrachloride → HCID 69899527, compound

HRID 1884229Notes

Reaction equation

HRID 1884229 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:13][C:14](=[O:31])[C:15]([C:21]2[CH:30]=[CH:29][C:28]3[CH2:27][CH2:26][CH2:25][CH2:24][C:23]=3[CH:22]=2)=[CH:16][O:17][CH2:18][C:19]#[CH:20])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(=O)([O-])[O-].[K+].[K+].C(Cl)(Cl)(Cl)[Cl:57]>O>[Cl:57][C:20]#[C:19][CH2:18][O:17][CH:16]=[C:15]([C:21]1[CH:30]=[CH:29][C:28]2[CH2:27][CH2:26][CH2:25][CH2:24][C:23]=2[CH:22]=1)[C:14]([NH:13][CH2:12][CH2:11][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)=[O:31]

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 11430Potassium CarbonateHCID 2724141Tetrabutylammonium FluorideHCID 86589992HCID 86589992, compound

Product 1

HCID 69899527HCID 69899527, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Three hundred milligrams (300 mg) of N-[2-(3,4-dimethoxyphenyl)ethyl]-3-(2-propynyloxy)-2-(5,6,7,8-tetrahydronaphthalen-2-yl)acrylamide (0.716 mmol), 20 mg (0.0766 mmol) of tetrabutylammonium fluoride, 100 mg (0.716 mmol) of potassium carbonate and 2 ml of carbon tetrachloride were mixed and stirred at room temperature. Water was added to the reaction mixture, which was followed by extracted with ethyl acetate, washed with 5% hydrochrolic acid and saturated brine subsequently, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography (eluent, hexane:ethyl acetate=1:1) to give 140 mg of 3-(3-chloro-2-propynyloxy)-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(5,6,7,8-tetrahydronaphthalen-2-yl)acrylamide (the present compound 1223).

Workup

  1. extractionby extracted with ethyl acetate
  2. washwashed with 5% hydrochrolic acid and saturated brine subsequently
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1ac3b83ef5024cb896f56b227b4236bf
Source dataset
uspto-grants-2004_07
Patent number
US06762321B2

Reaction notes

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