Dimethyl Sulfate → 2(5H)-Thiophenone, 4-methoxy-3,5-dimethyl-5-octyl-

HRID 1992568Notes

Reaction equation

[OH:1][C:2]1[C:6]([CH3:15])([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[S:5][C:4](=[O:16])[C:3]=1[CH3:17].S(OC)(O[CH3:22])(=O)=O>>[CH3:22][O:1][C:2]1[C:6]([CH3:15])([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[S:5][C:4](=[O:16])[C:3]=1[CH3:17]

Participants

Reactant 2

HCID 6497Dimethyl Sulfate

HCID 135411009348113-81-5

Product 1

HCID 114826192(5H)-Thiophenone, 4-methoxy-3,5-dimethyl-5-octyl-Yield 71%

Procedure

From 34 (40 mg, 0.16 mmol), KH (27 mg, 0.20 mmol, 30% in mineral oil) and dimethyl sulfate (30 μL, 0.31 mmol) following general procedure H was obtained 37 (30 mg, 71%). 1H NMR (300 MHz, CDCl3) δ 0.86 (t, J=7 Hz, 3H), 1.06-1.09 (m, 1H), 1.24 (s, 10H), 1.41-1.48 (m, 1H), 1.55 (s, 3H), 1.71-1.79 (m, 2H), 1.98 (s, 3H), 4.09 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 9.59, 14.1, 22.6, 25.2, 26.5, 29.2, 29.4, 29.6, 31.8, 38.9, 58.7, 59.8, 111.3, 180.2, 195.7. IR (NaCl) 2927, 1676, 1631, 1582 cm−1. Analysis Calculated for C15H26O2S: C, 66.6; H, 9.69; Found: C, 66.5; H, 9.67.

Sources & evidence

ORD record: ord-048ac6ed4c144625af70c397c0a59b3b
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07649012B2

Reaction notes

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