Propargyl alcohol → HCID 18446528, compound

HRID 1868317Notes

Reaction equation

HRID 1868317 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][C:6]=1[CH2:7][CH2:8][C:9]#[N:10].[CH2:11]([OH:14])[C:12]#[CH:13]>CCN(CC)CC.[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>[OH:14][CH2:11][C:12]#[C:13][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[CH2:7][CH2:8][C:9]#[N:10]

Participants

6

Reactant 2

HCID 7859Propargyl alcoholHCID 18446530HCID 18446530, compound

Product 1

HCID 18446528HCID 18446528, compoundYield 61.1%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 3-(2-bromo-thiophen-3-yl)-propionitrile 81 (0.5 g, 2.31 mmol), CuI (0.04 g, 0.23 mmol), PdCl2(PPh3)2 (0.08 g, 0.12 mmol) in NEt3 (6 mL) at room temperature was added propargyl alcohol (0.28 mL, 4.62 mmole) and the reaction mixture was stirred at 50° C. for 9 h. The mixture was concentrated in vacuo and purified by silica gel column chromatography (eluent: 50% EtOAc in hexane). The major fractions were combined and concentrated to give 82 (0.27 g) as a yellow syrup. 1H NMR (400 MHz, d6-DMSO) δ: 7.54 (d, J=5.0 Hz, 1H), 7.10 (d, J=5.0 Hz, 1H), 5.37 (t, J=6.0 Hz, 1H), 4.34 (d, J=6.0 Hz, 2H), 2.93 (t, J=7.0 Hz, 2H), 2.84 (t, J=7.0 Hz, 2H). MS (EI) m/z (M−OH+) 174.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. custompurified by silica gel column chromatography (eluent: 50% EtOAc in hexane)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-858f9f7c14d14cf9a3c4fb1abf1ebab2
Source dataset
uspto-grants-2009_12
Patent number
US07635695B2

Reaction notes

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