HCID 86608890, compound → 2(5H)-Thiophenone, 4-(4-chlorobutoxy)-5-methyl-5-octyl-

HRID 1992569Notes

Reaction equation

HRID 1992569 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])[CH:3]=1.I[CH:18]([CH3:22])[CH2:19][CH2:20][Cl:21]>>[Cl:21][CH2:20][CH2:19][CH2:18][CH2:22][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])[CH:3]=1

Participants

3

Reactant 2

HCID 86608890HCID 86608890, compoundHCID 1355380184-hydroxy-5-Methyl-5-octylthiophen-2(5H)-one

Product 1

HCID 114390022(5H)-Thiophenone, 4-(4-chlorobutoxy)-5-methyl-5-octyl-Yield 85%

Procedure

From 32 (47 mg, 0.18 mmol) and 3-iodo-1-chlorobutane (40 μL, 0.36 mmol) following general procedure H was obtained 41 (46 mg, 85%) after flash chromatography (20% EtOAc/Hexanes). 1H NMR (300 MHz, CDCl3) δ 0.86 (t, J=7 Hz, 3H), 1.07-1.27 (m, 1H), 1.24 (s, 10H) 1.48-1.51 (m, 1H), 1.62 (s, 3H), 1.75-1.82 (m, 2H), 1.89-1.98 (m, 4H), 3.59 (t, J=5.9 Hz, 2H), 3.95-3.98 (m, 2H), 5.28 (s, 1H); 13C NMR (75 MHz, CDCl3) δ 14.1, 22.6, 25.1, 26.0, 26.5, 29.0, 29.2, 29.3, 29.5, 29.7, 31.8, 44.1, 59.6, 71.7, 101.6, 186.1, 193.8. Analysis Calculated for C17H29C2S: C, 61.3; H, 8.78, Found: C, 61.9; H, 9.01.

Sources & evidence

ORD record
ord-0b473234278343f8a9e91cbfdd375a2e
Source dataset
uspto-grants-2010_01
Patent number
US07649012B2

Reaction notes

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