Triethylamine → HCID 15540938, compound

HRID 1489376Notes

Reaction equation

HRID 1489376 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[S:8][CH2:7][CH2:6][C:5]2([CH2:15][CH2:16][CH3:17])[CH2:12][CH2:13][CH3:14].C(N(CC)CC)C.[CH3:25][Si:26]([C:29]#[CH:30])([CH3:28])[CH3:27]>[Cu]I.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH2:12]([C:5]1([CH2:15][CH2:16][CH3:17])[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([C:30]#[C:29][Si:26]([CH3:28])([CH3:27])[CH3:25])[CH:3]=2)[S:8][CH2:7][CH2:6]1)[CH2:13][CH3:14]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 15540937HCID 15540937, compound2×

Product 1

HCID 15540938HCID 15540938, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalyst

Conditions

Temperature
0 °C

Procedure

A mixture of 2.04 g (6.54 mmol) of 6-bromo-4,4-dipropylthiochroman (Compound 29), 0.12 g(0.64 mmol) of copper (I) iodide and 5.4 g (54 mmol) of triethylamine was degassed using argon for 15 minutes at -78° C. To the suspension was added 1.95 g (19.8 mmol) of (trimethylsilyl)acetylene then 0.41 g (58 mmol) of bis(triphenylphosphine]palladium (II) chloride. The solution was degassed with argon for an additional 5 minutes and the resulting mixture was allowed to warm to 0° C. The tube was sealed and the mixture heated to 55° C. for 15 hours.

Workup

  1. customwas degassed
  2. customfor 15 minutes
  3. customat -78° C
  4. customThe solution was degassed with argon for an additional 5 minutes
  5. customThe tube was sealed
  6. temperaturethe mixture heated to 55° C. for 15 hours

Sources & evidence

ORD record
ord-21018f66e66c46688cad627ef02fa45c
Source dataset
uspto-grants-1997_10
Patent number
US05677451

Reaction notes

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