Isothiochromanone → HCID 19754938, compound

HRID 1588895Notes

Reaction equation

[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH2:3][S:2]1.[F:12][B-:13]([F:16])([F:15])[F:14].[CH2:17]([O+](CC)CC)[CH3:18]>>[F:12][B-:13]([F:16])([F:15])[F:14].[CH2:17]([S+:2]1[CH2:3][C:4](=[O:11])[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:1]1)[CH3:18]

Participants

Reactant 2

HCID 78150Isothiochromanone

HCID 2723982Triethyloxonium tetrafluoroborate

Product 1

HCID 19754938HCID 19754938, compoundYield 50%

Procedure

1.642 g (10 mmol) isothiochroman-4-one (J. Am. Chem. Soc. 1973, 95, 2923) was alkylated with triethyloxonium tetrafluoroborate (10 mmol, 1M in methylene chloride) according to the method described for compound B2. Recrystallization in ethanol gave 1.26 g (50%) of D1 as white crystals; mp=89.6° C. 1H-NMR (acetone-d6) δ 7.65-8.14 (4 H, m, Ar--H), 5.23 (1 H, d, J=16.1 Hz, --CHH--C(O)--), 5.03 (1 H, d, J=16.1 Hz, --CHH--C(O)--), 4.80 (1 H, d, J=17.2 Hz, --CHH--Ar), 4.55 (1 H, dd, J=2.0 and 17.2 Hz, --CHH--Ar), 3.45-3.85 (2 H, m, >S+ --CH2 --CH3), 1.55 (3 H, t, J=7.5 Hz, >S+ --CH2 -- CH3); 13C-NMR (acetone-d6) δ 183.64, 136.04, 131.78, 130.97, 130.75, 130.51, 128.93, 40.06, 34.45, 34.40, 8.85; UV-absorption max. (ethanol): 254, 293 nm; Anal. Calcd for C11H13BF4OS: C, 47.2%; H, 4.7%; S, 11.5%. Found: C, 47.3%; H, 4.6%; S, 11.5%.

Workup

customRecrystallization in ethanol

Sources & evidence

ORD record: ord-5fe7564cb0fe409ea5b76ab995f8bc85
Source dataset: uspto-grants-1993_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05223591

Reaction notes

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