Triethylamine → HCID 67145871, compound

HRID 1810613Notes

Reaction equation

HRID 1810613 reaction equation
C(N(CC)CC)C.Br[C:9]1[CH:14]=[CH:13][C:12](/[C:15](/[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:16]/[CH2:17][O:18][C:19]2[CH:30]=[CH:29][C:22]([O:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])=[C:21]([CH3:31])[CH:20]=2)=[CH:11][CH:10]=1.[CH2:38]([N:41]1[CH2:46][CH2:45][O:44][CH2:43][CH2:42]1)[C:39]#[CH:40]>O1CCCC1.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:31][C:21]1[CH:20]=[C:19]([O:18][CH2:17]/[CH:16]=[C:15](/[C:12]2[CH:13]=[CH:14][C:9]([C:40]#[C:39][CH2:38][N:41]3[CH2:46][CH2:45][O:44][CH2:43][CH2:42]3)=[CH:10][CH:11]=2)\[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:30]=[CH:29][C:22]=1[O:23][CH2:24][C:25]([O:27][CH3:28])=[O:26]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 4129414-(2-Propyn-1-yl)morpholineHCID 131728880HCID 131728880, compound

Product 1

HCID 67145871HCID 67145871, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Dry triethylamine (8 mL), copper(I) iodide (29 mg, 0.152 mmol) and tetrakis(triphenylphosphine)palladium (68 mg, 0.059 mmol) were added to a degassed solution of the above ester (448 mg, 0.931 mmol) and N-propargylmorpholine (291 mg, 2.32 mmol) in dry tetrahydrofuran (18 mL). In atmosphere of argon, the resulting mixture was heated at 50° C. for 10 h, cooled down and subsequently evaporated in vacuo. The residue was dissolved in dichloromethane (20 mL); the solution was washed with water (3×10 mL), dried with anhydrous magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography (silica gel Fluka 60, hexanes/ethyl acetate 4:1-1:1) yielding methyl (E)-[2-methyl-4-[3-[4-[3-(morpholin-4-yl)propynyl]phenyl]-3-phenylallyloxy]phenoxy]acetate as an oil.

Workup

  1. temperaturecooled down
  2. customsubsequently evaporated in vacuo
  3. dissolutionThe residue was dissolved in dichloromethane (20 mL)
  4. washthe solution was washed with water (3×10 mL)
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography (silica gel Fluka 60, hexanes/ethyl acetate 4:1-1:1)

Sources & evidence

ORD record
ord-b96733fd14bc4dd4a2f9cb787b4c6e73
Source dataset
uspto-grants-2013_01
Patent number
US08362016B2

Reaction notes

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