Dichloromethane → HCID 19105539, compound

HRID 373420Notes

Reaction equation

HRID 373420 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]([C:14]#[CH:15])[CH:8]=2)[S:3]1.I[C:17]1[CH:27]=[CH:26][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][CH:18]=1.C(Cl)Cl>C(N(CC)CC)C>[CH2:24]([O:23][C:21](=[O:22])[C:20]1[CH:26]=[CH:27][C:17]([C:15]#[C:14][C:7]2[CH:8]=[C:9]3[C:4](=[CH:5][CH:6]=2)[S:3][CH:2]([CH3:1])[CH2:11][C:10]3([CH3:12])[CH3:13])=[CH:18][CH:19]=1)[CH3:25]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 142891Ethyl 4-iodobenzoateHCID 19105556HCID 19105556, compound2×

Product 1

HCID 19105539HCID 19105539, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
55 °C

Procedure

A solution of 55 mg (0.26 mmol) of 2,4,4-trimethyl-6-ethynyl-thiochroman (Compound 55) and 70.5 mg (0.26 mmol) of ethyl 4-iodo benzoate (29) in 1.5 ml of distilled triethylamine was placed in a heavy walled tube. Argon was bubbled through the mixture for 20 minutes under slightly reduced pressure. To the mixture was added 18 mg (0.051 mmol) of bis triphenylphosphine palladium (II) chloride and 9.7 mg (0.051 mmol) of cuprous iodide. The tube was then sealed and the mixture was stirred at 55 degrees C. for 72 hours. The mixture was then cooled to room temperature. The reaction mixture was diluted wth CH2Cl2 and treated with a small amount of silica. The solvent was then removed in-vacuo and the residue was subjected to flash chromatography (silica; 1.5% EtOAc/Hexanes) to give the title compound as a white crystalline solid. PMR(CdCl3): 1.25 (3H, s), 1.35 (3H, d, J=6.6 Hz), 1.37-1.44 (6H, m), 1.75 (1H, t, J=13 Hz), 1.88 (1H, dd, J=13 Hz, 3.5 Hz), 3.40-3.50 (1H, m), 4.38 (2H, q, J=7Hz), 7.17 (1H, dd, J=8.1 Hz, 1.8 Hz), 7.26 (1H, d, J=1.5 Hz), 7.33 (1H, J=8.1 Hz), 7.55 (2H, d, J=8.4 Hz, 8.01 (2H, d, J=8.4 Hz).

Workup

  1. customArgon was bubbled through the mixture for 20 minutes under slightly reduced pressure
  2. customThe tube was then sealed
  3. temperatureThe mixture was then cooled to room temperature
  4. additiontreated with a small amount of silica
  5. customThe solvent was then removed in-vacuo

Sources & evidence

ORD record
ord-15302995e9cf40d2948360c863b591a4
Source dataset
uspto-grants-1992_11
Patent number
US05162546

Reaction notes

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