Diisopropylamine → 289652-61-5

HRID 1971640Notes

Reaction equation

HRID 1971640 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][CH:6]=1.[C:7]([OH:11])#[C:8][CH2:9][CH3:10].C(NC(C)C)(C)C.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>O1CCOCC1.C1(C)C=CC=CC=1.O.[Cu]I>[S:3]1[CH:4]=[CH:5][CH:6]=[C:2]1[C:10]#[C:9][CH2:8][CH2:7][OH:11]

Participants

9

Reactant 4

HCID 7912DiisopropylamineHCID 138512-BromothiopheneHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 15129470HCID 15129470, compound

Product 1

HCID 12181232289652-61-5Yield 75.9%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1.2 g of 2-bromothiophene and 0.9 g of butynol in 15 ml of degassed dioxane were added 100 mg of PdCl2(PheCN)2, 50 mg of CuI, 1 ml of diisopropyl amine, 750 μl of a 1M solution of tri-tert-butyl phosphine in toluene. The mixture was stirred under N2 atmosphere for 16 hr and then diluted with 50 ml of water and extracted with ethyl acetate. The organic layers were combined and washed with water, dried and concentrated. The residue was chromatographed using a gradient of heptane/ethyl acetate as eluent, to provide 850 mg of 1a; Rf (heptane/ethyl acetate 1/1) 0.50. NMR (CDCl3) δ 1.83 (t, 1, OH), 2.72 (t, 2, CH2), 3.83 (q, 2, CH2), 6.95, 7.16, 7.20 (3×m, 3, thiophene-H).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was chromatographed

Sources & evidence

ORD record
ord-722d3864c98b41ce93f7eb094cb455dc
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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