Triethylamine → Ethyl 4-[2-(4,4-dibutylthiochroman-6-yl)-ethyn-1-yl]benzoate

HRID 129616Notes

Reaction equation

[CH2:1]([C:5]1([CH2:17][CH2:18][CH2:19][CH3:20])[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]#[CH:16])[CH:13]=2)[S:8][CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].C(N([CH2:26][CH3:27])CC)C.IC1[CH:39]=[CH:38][C:32]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:31]N=1>[Cu]I>[CH2:1]([C:5]1([CH2:17][CH2:18][CH2:19][CH3:20])[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]#[C:16][C:27]3[CH:26]=[CH:31][C:32]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:38][CH:39]=3)[CH:13]=2)[S:8][CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 55 °C

Procedure

A mixture of 0.234 g (0.82 mmol) of (4,4-dibutylthiochroman-6-yl)acetylene (Compound 35), 21 mg (0.11 mmol) of copper (I) iodide, and 1.45 g (14 mmol) of triethylamine were degassed with argon for 15 min. To the suspension was added 0.49 g (1.8 mmol) of ethyl 4-iodobenzoate (Compound 21) and then 0.065 g (0.09 mmol) of bis(triphenyliphosphine)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 20 hours.

Workup

customwere degassed with argon for 15 min
customThe suspension was degassed with argon for an additional 5 minutes
customthe tube was sealed

Sources & evidence

ORD record: ord-e69551b5fcd0496aa84a521baa3d08a8
Source dataset: uspto-grants-1995_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05468879

Reaction notes

Loading…