Butylamine → HCID 86746681, compound

HRID 1109019Notes

Reaction equation

HRID 1109019 reaction equation
[Cl:1]/[CH:2]=[CH:3]\Cl.C(N)CCC.[O:10]([CH2:17][C:18]#[CH:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>[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.C1COCC1>[Cl:1]/[CH:2]=[CH:3]\[C:19]#[C:18][CH2:17][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 3

HCID 8007ButylamineHCID 83613(Prop-2-ynyloxy)benzeneHCID 643833cis-1,2-Dichloroethylene

Product 1

HCID 86746681HCID 86746681, compoundYield 67.6%

Reagents, catalysts & solvents 3

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

Procedure

To a 1 L flask under Argon was added CuI (7.86 g, 41.2 mmol) and Pd(PPh3)4 (5 g, 4.3 mmol). The catalyst was covered With 600 mL of degassed THF, cis-1,2-dichloroethylene (50 g, 516 mmol), and butylamine (68 mL, 688 mmol). Phenoxy-2-propyne (45g, 340 mmol) was added neat over 10 min and the reaction mixture stirred for 5.5 h. Air was bubbled through the reaction mixture for 15 min and the reaction filtered through a pad of celite and washed with pentane. The filtrate was washed with water and brine and the aqueous fractions extracted with ether. The organic fractions were combined, dried (MgSO4), filtered through celite and concentrated. The residue was chromatographed over silica gel (hexane) to give 44.3 g of a yellow oil (67%).

Workup

  1. customAir was bubbled through the reaction mixture for 15 min
  2. filtrationthe reaction filtered through a pad of celite
  3. washwashed with pentane
  4. washThe filtrate was washed with water and brine
  5. extractionthe aqueous fractions extracted with ether
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered through celite
  8. concentrationconcentrated
  9. customThe residue was chromatographed over silica gel (hexane)

Sources & evidence

ORD record
ord-80f10535f35a45659fa938ccadabead1
Source dataset
uspto-grants-1994_06
Patent number
US05318989

Reaction notes

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