Butyl Acetate → HCID 86679294, compound

HRID 1519736Notes

Reaction equation

HRID 1519736 reaction equation
[CH:1]([Si:4]([C:11]#[CH:12])([CH:8]([CH3:10])[CH3:9])[CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].Br[C:14]1[CH:15]=[C:16]([CH:19]=[O:20])[O:17][CH:18]=1.C(OCCCC)(C)=O>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.[Cu]I.C(OCC)(=O)C>[CH:8]([Si:4]([C:11]#[C:12][C:14]1[CH:15]=[C:16]([CH:19]=[O:20])[O:17][CH:18]=1)([CH:5]([CH3:6])[CH3:7])[CH:1]([CH3:3])[CH3:2])([CH3:10])[CH3:9]

Participants

7

Reactant 3

HCID 31272Butyl AcetateHCID 2734682(Triisopropylsilyl)acetyleneHCID 27570104-Bromo-2-furaldehyde

Product 1

HCID 86679294HCID 86679294, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Triisopropylsilylacetylene (9.0 mL) was added dropwise to a mixture of 4-bromofuran-2-carbaldehyde (2.0 g), PdCl2(PPh3)2 (0.40 g), CuI (0.22 g), TEA (7.9 mL) and AcOBu (20 mL) at 110 to 120° C. over the course of 6 hours in a nitrogen atmosphere, and then the mixture was stirred for 2 hours. After the reaction mixture was allowed to cool, ethyl acetate (50 mL), OH type silica gel (1.0 g), cellpure (1.2 g) and activated carbon (20 mg) were added. The insolubles were filtered out, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by OH type silica gel column chromatography (gradient elution with hexane/ethyl acetate=100/0→65/35) to obtain 4-[(triisopropylsilanyl)ethynyl]furan-2-carbaldehyde (black oil) (2.3 g, 72%).

Workup

  1. temperatureto cool
  2. filtrationThe insolubles were filtered out
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe resulting residue was purified by OH type silica gel column chromatography (gradient elution with hexane/ethyl acetate=100/0→65/35)

Sources & evidence

ORD record
ord-b953ee4598bd4b3384e4886a5d764e2c
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

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