Triethylamine → (4,4-Dibutylthiochroman-6-yl)(trimethylsilyl)acetylene

HRID 1376809Notes

Reaction equation

HRID 1376809 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([CH2:16][CH2:17][CH2:18][CH3:19])[CH2:12][CH2:13][CH2:14][CH3:15].C(N(CC)CC)C.[CH3:27][Si:28]([C:31]#[CH:32])([CH3:30])[CH3:29]>[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([CH2:16][CH2:17][CH2:18][CH3:19])[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([C:32]#[C:31][Si:28]([CH3:30])([CH3:29])[CH3:27])[CH:3]=2)[S:8][CH2:7][CH2:6]1)[CH2:13][CH2:14][CH3:15]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 183220116-Bromo-4,4-dibutylthiochroman2×

Product 1

HCID 18321992(4,4-Dibutylthiochroman-6-yl)(trimethylsilyl)acetylene

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 1.68 g (5.38 mmol) of 6-bromo-4,4-dibutylthiochroman (Compound 33), 0.28 g (1.5 mmol) of copper (I) iodide and 2.5 g (25 mmol) of triethylamine was degassed with argon for 15 minutes at -78° C. To the suspension was added 1.18 g (71 mmol) of (trimethylsilyl)acetylene and 0.24 g (0.3 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 was heated to 55° C. for 22 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 was heated to 55° C. for 22 hours

Sources & evidence

ORD record
ord-6daf9e1b91d649f9b478f6227dd49b35
Source dataset
uspto-grants-1997_09
Patent number
US05663347

Reaction notes

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