Potassium ethanethioate → HCID 178477070, compound

HRID 1824643Notes

Reaction equation

[C-:1]1([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]Br)[CH:5]=[CH:4][CH:3]=[CH:2]1.[CH-:23]1[CH:27]=[CH:26][CH:25]=[CH:24]1.[Fe+2:28].[C:29]([O-:32])(=[S:31])[CH3:30].[K+]>>[C:29]([S:31][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C-:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1)(=[O:32])[CH3:30].[CH-:23]1[CH:27]=[CH:26][CH:25]=[CH:24]1.[Fe+2:28]

Participants

Reactant 2

HCID 23670855Potassium ethanethioate

HCID 178419537HCID 178419537, compound

Product 1

HCID 178477070HCID 178477070, compoundYield 93%

Procedure

16-Ferrocenylhexadecyl bromide 26 (1.1 g, 2.3 mmol) was treated with potassium thioacetate (0.4 g, 3.5 mmol) for 20 h following the same procedure described for 27 to afford yellow crystals (1.0 g, 93%): mp 55–57° C.; 1H NMR δ 1.25 (s, 22H), 1.51 (m, 2H), 2.30 (m, 2H), 2.32 (s, 3H), 2.86 (m, 2H), 4.04 (s, 2H), 4.05 (s, 2H), 4.09 (s, 5H); 13C NMR δ 29.5, 29.8, 30.2, 30.3, 30.3, 31.8, 67.7, 68.8, 69.2, 90.0, 197.5; FAB-MS obsd 484.2518, calcd exact mass 484.2514; Anal. Calcd for C28H44FeOS: C, 69.40; H, 9.15; Found: C, 69.45; H, 9.07.

Sources & evidence

ORD record: ord-1b937d5b304140ecb61e398638a10be5
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07042755B1

Reaction notes

Loading…