Triethylamine → HCID 15296873, compound

HRID 129610Notes

Reaction equation

HRID 129610 reaction equation
[CH2:1]([C:3]1([CH2:15][CH3:16])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]#[CH:14])[CH:11]=2)[S:6][CH2:5][CH2:4]1)[CH3:2].C(N(CC)CC)C.I[C:25]1[CH:35]=[CH:34][C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:27][CH:26]=1>[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>[CH2:15]([C:3]1([CH2:1][CH3:2])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]#[C:14][C:25]3[CH:35]=[CH:34][C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:27][CH:26]=3)[CH:11]=2)[S:6][CH2:5][CH2:4]1)[CH3:16]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 142891Ethyl 4-iodobenzoate2×HCID 158953004,4-Diethyl-6-ethynyl-3,4-dihydro-2H-1-benzothiopyran

Product 1

HCID 15296873HCID 15296873, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
55 °C

Procedure

A mixture of 0.338 g (1.47 mmol) of (4,4-diethylthiochroman-6-yl)acetylene, 24 mg (0.13 mmol) of copper (I) iodide, and 2.54 g (25 mmol) of triethylamine were degassed with argon for 15 minutes. To the suspension was added 0.57 g (2.07 mmol) of ethyl 4-iodobenzoate (Compound 22) and then 0.12 g (0.17 mmol) of bis(triphenylphosphine)palladium (II) chloride. The suspension was degassed with argon for an additional 5 minutes, the tube was sealed and the mixture stirred at 55° C. for 16 hours.

Workup

  1. customwere degassed with argon for 15 minutes
  2. customThe suspension was degassed with argon for an additional 5 minutes
  3. customthe tube was sealed

Sources & evidence

ORD record
ord-9c4c1da7e30e4337b08b334e36764438
Source dataset
uspto-grants-1995_11
Patent number
US05468879

Reaction notes

Loading…