Tetrahydrofuran → 3-{4-[1-Ethyl-1-(6-methoxy-benzo[b]thiophen-2-yl)-propyl]-2-methyl-phenoxymethyl}-pentan-3-ol

HRID 599706

Reaction equation

HRID 599706 reaction equation
C[O:2][C:3](=O)[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([CH2:26][CH3:27])([C:15]2[S:19][C:18]3[CH:20]=[C:21]([O:24][CH3:25])[CH:22]=[CH:23][C:17]=3[CH:16]=2)[CH2:13][CH3:14])=[CH:8][C:7]=1[CH3:28].[CH2:30]1[CH2:34]OCC1.[CH2:35]([Mg]Br)[CH3:36]>[Cl-].N>[CH2:13]([C:12]([C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][C:3]([OH:2])([CH2:35][CH3:36])[CH2:30][CH3:34])=[C:7]([CH3:28])[CH:8]=1)([C:15]1[S:19][C:23]2[CH:22]=[C:21]([O:24][CH3:25])[CH:20]=[CH:18][C:17]=2[CH:16]=1)[CH2:26][CH3:27])[CH3:14]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 57835409{4-[1-Ethyl-1-(6-methoxy-benzo[b]thiophen-2-yl)-propyl]-2-methyl-phenoxy}-acetic acid methyl esterHCID 178418443HCID 178418443, compound

Product 1

HCID 578354013-{4-[1-Ethyl-1-(6-methoxy-benzo[b]thiophen-2-yl)-propyl]-2-methyl-phenoxymethyl}-pentan-3-olYield 56%

Reagents, catalysts & solvents 1

HCID 20976574Ammonia chlorideSolvent

Procedure

To a mixture of {4-[1-ethyl-1-(6-methoxy-benzo[b]thiophen-2-yl)-propyl]-2-methyl-phenoxy}-acetic acid methyl ester (1.50 g, 3.64 mmol) and THF (20 mL) is added ethyl magnesium bromide (3.0 mL, 9.1 mmol, 3M in THF). The solution is heated at a reflux for 3 h, diluted with saturated ammonia chloride solution (80 mL), extracted with diethyl ether (2×75 mL), dried over MgSO4, filtered, and concentrated. The residue is purified by silica gel chromatography (10% to 30% EtOAc gradient) to give the title compound (0.90 g, 2.04 mmol, 56%). 1H NMR (CDCl3), δ 0.75 (t, J=7.6 Hz, 6H), 0.95 (t, J=7.4 Hz, 6H), 1.68 (q, J=14.8, 7.5 Hz, 4H), 2.13-2.24 (m, 7H), 3.81 (s, 2H), 3.86 (s, 3H), 6.73 (dd, J=8.2 Hz, 1H), 6.89 (dd, J=8.8, 2.6 Hz, 1H), 7.06 (s, 2H), 7.09 (dd, J=8.4, 2.5 Hz, 1H), 7.17 (d, J=2.7 Hz, 1H), 7.55 (d, J=8.8 Hz, 1H). LC/MS (m/z): calcd. for C27H37O3S (M+H)+: 441.3; found: 441.2.

Workup

  1. temperatureThe solution is heated at
  2. temperaturea reflux for 3 h
  3. extractionextracted with diethyl ether (2×75 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is purified by silica gel chromatography (10% to 30% EtOAc gradient)

Sources & evidence

ORD record
ord-3ac1e95e4b32479fa3936e60cc8a7767
Source dataset
uspto-grants-2011_03
Patent number
US07897789B2

Linked notes

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