Tetrahydrofuran → HCID 57890205, compound

HRID 1819928Notes

Reaction equation

HRID 1819928 reaction equation
C[O:2][C:3](=O)[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([CH2:21][CH3:22])([C:15]2[S:16][CH:17]=[C:18]([CH3:20])[CH:19]=2)[CH2:13][CH3:14])=[CH:8][C:7]=1[CH3:23].[CH2:25]([Mg]Br)[CH3:26].[CH2:29]1COC[CH2:30]1>>[CH2:13]([C:12]([C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][C:3]([OH:2])([CH2:25][CH3:26])[CH2:29][CH3:30])=[C:7]([CH3:23])[CH:8]=1)([C:15]1[S:16][CH:17]=[C:18]([CH3:20])[CH:19]=1)[CH2:21][CH3:22])[CH3:14]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 57890146HCID 57890146, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 57890205HCID 57890205, compoundYield 87%

Conditions

Temperature
0 °C

Procedure

{4-[1-Ethyl-1-(4-methyl-thiophen-2-yl)-propyl]-2-methyl-phenoxy}acetic acid methyl ester (5.52 g, 15.95 mmol) is dissolved in THF (50 mL). The solution is cooled to 0° C., and treated with Ethyl magnesiumbromide (3.0 M, 13.3 mL) in a dropwise fashion. The reaction is stirred at 0° C. for 10 m, and refluxed for 3 h. It is cooled to 0° C., quenched with sat. NH4Cl (50 mL), then 1.0 M HCl (30 mL) is added. It is extracted with EtOAc (2×100 mL), dried and concentrated. The crude product is purified by chromatography to give the titled compound (5.22 g, 13.96 mmol, 87%). 1H NMR (CD3Cl3), δ 0.71 (t, J=7.4 Hz, 6H), 0.95 (t, J=7.1 Hz, 6H), 1.62-1.73 (m, 4H), 2.04-2.14 (m, 4H), 2.21 (s, 6H), 3.81 (s, 2H), 6.59-6.61 (m, 1H), 6.69-6.74 (m, 2H), 7.02-7.08 (m, 2H). LC/MS (m/z): calcd for C23H35O2S (M+H)+:375.6; found: 375.3.

Workup

  1. temperaturerefluxed for 3 h
  2. temperatureIt is cooled to 0° C.
  3. customquenched with sat. NH4Cl (50 mL)
  4. addition1.0 M HCl (30 mL) is added
  5. extractionIt is extracted with EtOAc (2×100 mL)
  6. customdried
  7. concentrationconcentrated
  8. customThe crude product is purified by chromatography

Sources & evidence

ORD record
ord-242830405a974cde80be3d03316dbf31
Source dataset
uspto-grants-2009_10
Patent number
US07601850B2

Reaction notes

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