Diethylamine → HCID 15199167, compound

HRID 2260880Notes

Reaction equation

HRID 2260880 reaction equation
[CH:1](Br)=[CH2:2].N(CC)CC.[CH2:9]([S:16]/[C:17](=[CH:20]\[CH:21]=[C:22](/[S:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)\[C:23]#[C:24][C:25]#[C:26][CH3:27])/[C:18]#[CH:19])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1C=CC=CC=1.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:9]([S:16]/[C:17](=[CH:20]\[CH:21]=[C:22](/[S:28][CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)\[C:23]#[C:24][C:25]#[C:26][CH3:27])/[C:18]#[C:19][CH:1]=[CH2:2])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 3

HCID 8021DiethylamineHCID 11641BromoetheneHCID 11783952HCID 11783952, compound

Product 1

HCID 15199167HCID 15199167, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 241BenzeneSolvent

Procedure

Vinyl bromide (0.5 mL, excess) was condensed into a flask under argon, followed by addition of CuI (7.2 mg, 0.015 mmol), (Ph3P)2PdCl2 (26 mg, 0.0376 mmol) and Et2NH (3 mL). Compound 10 (145 mg, 0.376 mmol) in benzene (10 mL) was added at 5° C. and the mixture was stirred in the dark for 16 h. Benzene was removed in vacuo, the residue was dissolved in CH2Cl2 (10 mL), washed with NH4Cl solution (2×15 ml) and water (15 mL), dried (MgSO4), concentrated in vacuo, and the residue purified by flash column chromatography (1:5 CH2Cl2 :hexanes) giving 11 as a yellow-green oil (109 mg, yield 70%): EI-MS, m/z 410 (M+), NH3CI-MS, m/z 428 (MNH4 +); UV (CH2Cl2) λ max 403; IR (CH2Cl2) 2226 (m), 2193 (w), 2142 (w) (all C=C), 1602 (m, C=C) cm-1 ; 1H NMR δ 7.1-7.3 (m, 10H), 6.95 (d, J=17.7, 2.1 Hz, 1 H), 5.49 (dd, J=11.1, 2.1 Hz, 1 H), 4.03 (s, 2 H), 4.02 (s, 2 H), 1.96 (s, 3 H); 13C NMR δ 116-138 (several), 94.90, 88.69, 84.46, 80.94, 72.69, 64.46, 37.52, 4.99.

Workup

  1. customcondensed into a flask under argon
  2. customBenzene was removed in vacuo
  3. dissolutionthe residue was dissolved in CH2Cl2 (10 mL)
  4. washwashed with NH4Cl solution (2×15 ml) and water (15 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customthe residue purified by flash column chromatography (1:5 CH2Cl2 :hexanes)

Sources & evidence

ORD record
ord-57e289a8f78a4e0cb1af9da9ae547789
Source dataset
uspto-grants-1995_12
Patent number
US05478959

Reaction notes

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