Butylamine → HCID 86746682, compound

HRID 1109020Notes

Reaction equation

HRID 1109020 reaction equation
Cl/[CH:2]=[CH:3]\[C:4]#[C:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(N)CCC.[CH3:19][Si:20]([C:23]#[CH:24])([CH3:22])[CH3:21]>[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>[O:7]([CH2:6][C:5]#[C:4]/[CH:3]=[CH:2]\[C:24]#[C:23][Si:20]([CH3:22])([CH3:21])[CH3:19])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 3

HCID 8007ButylamineHCID 66111TrimethylsilylacetyleneHCID 86746681HCID 86746681, compound

Product 1

HCID 86746682HCID 86746682, compoundYield 62.7%

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 (5.24 g, 27 mmol) and Pd(PPh3)4 (4.9 g, 4 mmol) and the catalyst covered with 500 mL of degassed THF. To this solution was added the product of step (a) (42.7 g, 220 mmol) and degassed butylamine (44 mL, 440 mmol). To this solution was added trimethylsilyl acetylene (29 g, 290 mmol) and the reaction mixture was stirred for 7 h. Air was bubbled through the solution for 15 min and the reaction mixture filtered through celite and washed with pentane. The filtrate was washed several times with water and the aqueous fractions extracted with ether. The organic fractions were combined, dried (MgSO4) and concentrated. The residue was chromatographed over silica gel (hexane) to give 35.1 g of a tan oil (62%).

Workup

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

Sources & evidence

ORD record
ord-c3ee1bddcd05494093e35ebdd5583954
Source dataset
uspto-grants-1994_06
Patent number
US05318989

Reaction notes

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