Triethylamine → HCID 77230289, compound

HRID 1455707Notes

Reaction equation

HRID 1455707 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6].C(N(CC)CC)C.[CH:19]#[C:20][CH2:21][CH2:22][CH2:23][CH3:24]>C1COCC1.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>[C:19]([C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6])#[C:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 127321-HexyneHCID 14943763-iodo-4-methoxybenzaldehyde

Product 1

HCID 77230289HCID 77230289, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-iodo-4-methoxybenzaldehyde (5.2 g, 20 mmol), tetrakis(triphenylphosphine)palladium (0.29 g), Cul (0.38 g, 2 mmol) and triethylamine (5 ml) in THF (25 ml) is cooled to +10° C., and 1-hexyne (3.5 ml, 30.5 mmol) is then added. The cooling bath is removed, and the temperature of the reaction mixture rises slowly to +30° C. before decreasing slowly. 3 hours after the end of the addition, the crude reaction product is concentrated to dryness, and the residue obtained is purified by flash chromatography on silica (15/85 ethyl acetate/heptane). 4.1 g (yield: 95%) of the expected product are obtained.

Workup

  1. temperatureis cooled to +10° C.
  2. customThe cooling bath is removed
  3. customrises slowly to +30° C.
  4. addition3 hours after the end of the addition
  5. customthe crude reaction product
  6. concentrationis concentrated to dryness
  7. customthe residue obtained
  8. customis purified by flash chromatography on silica (15/85 ethyl acetate/heptane)

Sources & evidence

ORD record
ord-ce6153a227f2452ca5e9ca7e8f312dc4
Source dataset
uspto-grants-2009_01
Patent number
US07482484B2

Reaction notes

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