Acetic Acid → HCID 12672451, compound

HRID 544754Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:18])[CH:10]=[C:11]([S:16][CH3:17])[CH2:12][C:13](=O)[CH3:14])=[CH:5][CH:4]=1.[F:19][B-:20]([F:23])([F:22])[F:21].[H+].O.C(O)(=O)C>ClCCCl>[F:19][B-:20]([F:23])([F:22])[F:21].[CH3:14][C:13]1[CH:12]=[C:11]([S:16][CH3:17])[CH:10]=[C:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[O+:18]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of this 1-(4-methoxyphenyl)-3-methylthio-2-hexen-1,5-dione (2.0 g, 7.57 mmol) in 1,2-dichloroethane (20 ml) was added tetrafluoroboric acid (10 ml, 48%). The mixture was stirred for four hours at 50° C. during which time a dense yellow solid formed. After addition of water (25 ml) and filtration, crystallization from acetic acid gave pale yellow needles of 2-methyl-4-methylthio 6-(4-methoxyphenyl)pyrylium tetrafluoroborate: 2.2 g (87%), m.p. 207°-210° C. (decomp), IR (KBr)νCO +1625 cm-1 ; NMR(DMSO-d6)δ8.34 (s,1, aromatic), 8.29 (d,2, J=9.0 Hz, aromatic), 7.80 (br. 3, 1, aromatic), 7.18 (d, 2, J=9.0 Hz, aromatic) 3.97 (s, 3, OCH3), 2.91 (s, 3, SCH3), (s, 3, CH3); M.+ 246 (100).

Workup

customformed

Sources & evidence

ORD record: ord-9d7628d55adf489db1e56d99ca56a190
Source dataset: uspto-grants-1984_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04451659

Reaction notes

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