Triethylamine → HCID 67826604, compound

HRID 373419Notes

Reaction equation

HRID 373419 reaction equation
[CH3:1][CH:2]1[CH2:11][C:10]([CH3:13])([CH3:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7](Br)[CH:8]=2)[S:3]1.[CH3:15][Si:16](C#C)([CH3:18])[CH3:17].[CH2:21](N(CC)CC)[CH3:22]>[Pd](Cl)Cl>[CH3:21][C:22]#[C:1][CH:2]1[CH2:11][C:10]([CH3:13])([CH3:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Si:16]([CH3:18])([CH3:17])[CH3:15])[CH:8]=2)[S:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 19105565HCID 19105565, compound2×

Product 1

HCID 67826604HCID 67826604, compound

Reagents, catalysts & solvents 1

HCID 24290Palladium ChlorideCatalyst

Conditions

Temperature
55 °C

Procedure

A solution of 201 mg (74 mmol) of 2,4,4-trimethyl-6-bromo-thiochroman (Compound 53) in 1 ml of distilled triethylamine was placed in a heavy walled tube and degassed. The mixture was then treated under argon with 0.53 ml (3.72 mmol) of trimethylsilylacetylene and a powdered mixture of 52 mg (0.074 mmol) of bis-triphenylhosphine palladium (II) chloride and 28 mg (0.15 mmol) of cuprous idodide. The reaction mixture was placed under argon and the tube was sealed. The mixture was heated at 55 degrees C. for 2 hours. The mixture was cooled to room temperature and filtered through celite and the residue washed with CH2Cl2. The filtrate was concentrated in-vacuo and the residue was purified by flash chromatography (silica; hexanes) to give the title compound as a yellow oil. PMR (CDCl3): & 0.24 (9H, s), 1.22 (3H, s), 1.33 (3H, d, J=6.6 Hz), 1.37 (3H, s), 1.71 (1H, t, J~13.0 Hz) 1.86 (1H, dd, J~13.0 Hz, 3.0 Hz) 3.38-3.50 (1H, m), 7.07 (1H, dd, J=8.1 Hz, 1.8Hz), 7.18 (1H, d, J=1.8 Hz), 7.26 (1H, d, J=8.1 HZ)

Workup

  1. customdegassed
  2. customthe tube was sealed
  3. temperatureThe mixture was cooled to room temperature
  4. filtrationfiltered through celite
  5. washthe residue washed with CH2Cl2
  6. concentrationThe filtrate was concentrated in-vacuo
  7. customthe residue was purified by flash chromatography (silica; hexanes)

Sources & evidence

ORD record
ord-93265748076a4a1c8c223458ff8c1c3e
Source dataset
uspto-grants-1992_11
Patent number
US05162546

Reaction notes

Loading…