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

HRID 1992570Notes

Reaction equation

HRID 1992570 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.I[CH:16]([CH3:20])[CH2:17][CH2:18][Cl:19]>>[Cl:19][CH2:18][CH2:17][CH2:16][CH2:20][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 86608890HCID 86608890, compoundHCID 135423465646517-41-1

Product 1

HCID 112551732(5H)-Thiophenone, 4-(4-chlorobutoxy)-5-hexyl-5-methyl-Yield 75%

Procedure

From 33 (36 mg, 0.17 mmol) and 3-iodo-1-chlorobutane (40 μL, 0.34 mmol) following general procedure H was obtained 42 (32 mg, 75%) after flash chromatography (20% EtOAc/Hexanes). 1H NMR (400 MHz, CDCl3) δ 0.86 (t, J=5.1 Hz, 3H), 1.09-1.14 (m, 1H), 1.25 (s, 6H), 1.44-1.53 (m, 1H), 1.63 (s, 3H), 1.77-1.85 (m, 2H), 1.90-2.00 (m, 4H), 3.59 (t, J=4.5 Hz, 2H), 3.95-3.99 (m, 2H), 5.28 (s, 1H). 13C NMR (75 MHz, CDCl3) δ 13.7, 22.3, 25.1, 26.1, 26.4, 29.1, 29.1, 31.5, 39.0, 43.9, 59.5, 71.6, 101.5, 185.9, 192.9. IR (NaCl) 2927, 1683, 1607 cm−1. Analysis Calculated for C15H25C2S: C, 59.1; H, 8.27; Found: C, 59.3; H, 8.39.

Sources & evidence

ORD record
ord-383f82d1651c4361b35ac814503db5c6
Source dataset
uspto-grants-2010_01
Patent number
US07649012B2

Reaction notes

Loading…