Propargyl alcohol → [4-(3-Hydroxy-1-propyn-1-yl)-2-methylphenyl]-4-morpholinylmethanone

HRID 1017786Notes

Reaction equation

HRID 1017786 reaction equation
Br[C:2]1[CH:15]=[CH:14][C:5]([C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[O:7])=[C:4]([CH3:16])[CH:3]=1.[CH2:17]([OH:20])[C:18]#[CH:19].C(N(CC)CC)C>C(#N)C.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.[Cu]I>[OH:20][CH2:17][C:18]#[C:19][C:2]1[CH:15]=[CH:14][C:5]([C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[O:7])=[C:4]([CH3:16])[CH:3]=1

Participants

7

Reactant 3

HCID 7859Propargyl alcoholHCID 8471TriethylamineHCID 18404846HCID 18404846, compound

Product 1

HCID 18404856[4-(3-Hydroxy-1-propyn-1-yl)-2-methylphenyl]-4-morpholinylmethanone

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

Prepared analogously to Example 1g from N-(4-bromo-2-methyl-benzoyl)-morpholine, propargyl alcohol, tetrakis(triphenylphosphine)palladium(0), copper(I)iodide and triethylamine in acetonitrile.

Sources & evidence

ORD record
ord-1508a5b8eb9a43d9ab91d9ec514541bb
Source dataset
uspto-grants-2002_11
Patent number
US06479524B1

Reaction notes

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