Dimethyl Sulfate → 2(5H)-Thiophenone, 5-hexyl-4-methoxy-5-methyl-

HRID 1992567Notes

Reaction equation

HRID 1992567 reaction equation
[OH:1][C:2]1[C:6]([CH3:13])([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[S:5][C:4](=[O:14])[CH:3]=1.S(OC)(O[CH3:19])(=O)=O>>[CH3:19][O:1][C:2]1[C:6]([CH3:13])([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[S:5][C:4](=[O:14])[CH:3]=1

Participants

3

Reactant 2

HCID 6497Dimethyl SulfateHCID 135423465646517-41-1

Product 1

HCID 114135452(5H)-Thiophenone, 5-hexyl-4-methoxy-5-methyl-Yield 58%

Procedure

From 33 (40.3 mg, 0.19 mmol) and dimethyl sulfate (35 μL, 0.37 mmol) following general procedure H was obtained 36 (25 mg, 58%) after flash chromatography (15% EtOAc/Hexanes). 1H NMR (300 MHz, CDCl3) δ 0.86 (t, J=6.7 Hz, 3H), 1.08-1.13 (m, 1H), 1.24 (s, 6H), 1.35-1.39 (m, 1H), 1.61 (s, 3H), 1.75-1.82 (m, 2H), 3.81 (s, 3H), 5.30 (s, 1H); 13C NMR (75 MHz, CDCl3) δ 14.0, 22.5, 25.1, 26.4, 29.2, 31.5, 38.9, 59.4, 59.4, 101.3, 187.3, 193.8.

Sources & evidence

ORD record
ord-1963879cfcaa4ea4b27f85f2cc78cb82
Source dataset
uspto-grants-2010_01
Patent number
US07649012B2

Reaction notes

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