Potassium ethanethioate → HCID 178477069, compound

HRID 2111474Notes

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]Br)[CH:5]=[CH:4][CH:3]=[CH:2]1.[CH-:19]1[CH:23]=[CH:22][CH:21]=[CH:20]1.[Fe+2:24].[C:25]([O-:28])(=[S:27])[CH3:26].[K+]>>[C:25]([S:27][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:28])[CH3:26].[CH-:19]1[CH:23]=[CH:22][CH:21]=[CH:20]1.[Fe+2:24]

Participants

Reactant 2

HCID 23670855Potassium ethanethioate

HCID 178419536HCID 178419536, compound

Product 1

HCID 178477069HCID 178477069, compoundYield 93%

Procedure

12-Ferrocenyldodecyl bromide 25 (2.0 g, 4.6 mmol) was treated with potassium thioacetate (0.70 g, 6.0 mmol) for 20 h as described for 27 to form yellow crystals (1.8 g, 93%): mp 45-47° C.; 1H NMR δ 1.27 (s, 18H), 1.55 (m, 2H), 2.32 (m, 2H), 2.33 (s, 3H), 2.87 (m, 2H), 4.05 (s, 2H), 4.07 (s, 2H), 4.11 (s, 5H); 13C NMR δ 29.5, 29.8, 30.2, 30.3, 30.3, 31.3, 31.8, 67.7, 68.8, 69.2, 90.4, 196.8; FAB-MS obsd 428.1851, calcd exact mass 428.1836; Anal. Calcd for C24H36FeOS: C, 67.28; H, 8.47. Found: C, 67.25; H, 8.51.

Sources & evidence

ORD record: ord-3e8aeca8e3974376820fa8fd4be90bfc
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07518905B2

Reaction notes

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