Dimethylformamide → 2-{1-Ethyl-1-[4-(2-ethyl-2-hydroxy-butoxy)-3-methyl-phenyl]-propyl}benzo[b]thiophen-6-ol

HRID 599707Notes

Reaction equation

[CH2:1]([C:3]([C:17]1[CH:30]=[CH:29][C:20]([O:21][CH2:22][C:23]([OH:28])([CH2:26][CH3:27])[CH2:24][CH3:25])=[C:19]([CH3:31])[CH:18]=1)([C:6]1[S:10][C:9]2[CH:11]=[C:12]([O:15]C)[CH:13]=[CH:14][C:8]=2[CH:7]=1)[CH2:4][CH3:5])[CH3:2].CN(C=O)C>C(OCC)C>[CH2:1]([C:3]([C:6]1[S:10][C:9]2[CH:11]=[C:12]([OH:15])[CH:13]=[CH:14][C:8]=2[CH:7]=1)([C:17]1[CH:30]=[CH:29][C:20]([O:21][CH2:22][C:23]([CH2:24][CH3:25])([OH:28])[CH2:26][CH3:27])=[C:19]([CH3:31])[CH:18]=1)[CH2:4][CH3:5])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 3-{4-[1-ethyl-1-(6-methoxy-benzo[b]thiophen-2-yl)-propyl]-2-methyl-phenoxymethyl}-pentan-3-ol (0.80 g, 1.82 mmol) and DMF (10 mL) is added NaSEt (1.53 g, 18.15 mmol). The resulting solution is heated at 100° C. overnight, diluted with diethyl ether (50 mL), washed with water (3×50 mL), brine (50 mL), dried with MgSO4, filtered and concentrated. The resulting residue is purified by silica gel chromatography (10% to 40% EtOAc gradient) to give the title compound (0.67 g, 1.57 mmol, 87%). 1H NMR (CDCl3), δ 0.75 (t, J=7.2 Hz, 6H), 0.95 (t, J=7.4 Hz, 6H), 1.67 (q, J=15.1, 7.4 Hz, 4H), 2.12-2.24 (m, 7H), 3.82 (s, 2H), 6.73 (d, J=8.6 Hz, 1H), 6.79 (dd, J=9.0, 2.6 Hz, 1H), 6.79 (dd, J=9.0, 2.6 Hz, 1H), 7.00 (s, 1H), 7.05 (d, J=2.2 Hz, 1H), 7.08 (dd, J=8.2, 2.6 Hz, 1H), 7.11 (d, J=2.2 Hz, 1H), 7.49 (d, J=9.0 Hz, 1H). LC/MS (m/z): calcd. for C26H35O3S (M+H)+: 427.2; found: 427.1.

Workup

washwashed with water (3×50 mL), brine (50 mL)
dry with materialdried with MgSO4
filtrationfiltered
concentrationconcentrated
customThe resulting residue is purified by silica gel chromatography (10% to 40% EtOAc gradient)

Sources & evidence

ORD record: ord-9deeebb92d2f4fae83cd76665907428a
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897789B2

Reaction notes

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