Triethylamine → HCID 18321988, compound

HRID 1376803Notes

Reaction equation

HRID 1376803 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([CH2:14][CH3:15])[CH2:12][CH3:13].C(N(CC)CC)C.[CH3:23][Si:24]([C:27]#[CH:28])([CH3:26])[CH3:25]>[Cu]I.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:12]([C:5]1([CH2:14][CH3:15])[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([C:28]#[C:27][Si:24]([CH3:26])([CH3:25])[CH3:23])[CH:3]=2)[S:8][CH2:7][CH2:6]1)[CH3:13]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 15284306HCID 15284306, compound2×

Product 1

HCID 18321988HCID 18321988, 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 1.96 g (6.90 mmol) of 6-bromo-4,4-diethylthiochroman (Compound 25), 0.11 g (0.59 mmol) of copper (I) iodide and 4.36 g (4.31 mmol) of triethylamine was degassed with argon for 15 minutes at -78° C. To the suspension was added 6.95 g (71 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 with argon for 15 minutes at -78° C
  2. customThe solution was degassed with argon for an additional 5 minutes
  3. customThe tube was sealed
  4. temperaturethe mixture heated to 55° C. for 15 hours

Sources & evidence

ORD record
ord-b81504ca106c41d4a41ebebfc70627c2
Source dataset
uspto-grants-1997_09
Patent number
US05663347

Reaction notes

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