Diethyl Ether → {2-[Dimethyl(thiophen-2-yl)silyl]phenyl}methanol

HRID 2423270Notes

Reaction equation

HRID 2423270 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[Mg]Br.O1CC[CH2:10][SiH2:9]1.[CH3:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C(O[C:22](=[O:24])C)C.[CH2:25](OCC)C>>[OH:24][CH2:22][C:15]1[CH:14]=[CH:13][CH:18]=[CH:17][C:16]=1[Si:9]([CH3:10])([CH3:25])[C:2]1[S:1][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 21226206Ethyl acetate hexaneHCID 123209143HCID 123209143, compoundHCID 178418438HCID 178418438, compound

Product 1

HCID 11242115{2-[Dimethyl(thiophen-2-yl)silyl]phenyl}methanolYield 79%

Procedure

At 0° C., a solution of 2-thienylmagnesium bromide in THF (23 mL) [prepared from 2-bromothiophene (5.4 g, 33 mmol) and Mg (0.82 g, 34 mmol) was added to oxasilacyclopentane (7) (4.9 g, 30 mmol) in THF (10 mL) in accordance with Frisell, C.; Lawesson, S.-O. Org. Synth. Coll. Vol. 1972, 5, 642-644], and the resulting mixture was stirred at room temperature for 22 hours. The resulting mixture was diluted with diethylether and was filtered to remove unreacted magnesium. The filtrate was washed with a saturated NH4Cl aqueous solution, water, and brine, and then was dried over anhydrous MgSO4. After removal of the solvents under reduced pressure, the residue was purified by flash chromatography on silica gel, thereby obtaining (2-(hydroxymethyl)phenyl)dimethyl(2-thienyl)silane: 2d (5.9 g, yield of 79%) as a colorless oil, Rf: 0.21 (hexane-ethylacetate=5:1). 1H NMR (400 MHz, CDCl3) δ 7.64 (d, J=4.6 Hz, 1H), 7.57 (d, J=7.4 Hz, 1H), 7.48 (d, J=7.6 Hz, 1H), 7.44 (t, J=7.4 Hz, 1H), 7.34-7.28 (m, 2H), 7.20 (dd, J=4.6, 3.4 Hz, 1H), 4.64 (s, 2H), 1.47 (s, 1H), 0.68 (s, 6H); 13C NMR (101 MHz, CDCl3) δ 146.5, 138.5, 135.6, 135.3, 131.3, 130.2, 128.4, 128.2, 127.1, 65.3, 0.2; Anal. Calcd for C13H16OSSi; C, 62.85; H, 6.49. Found: C, 62.96; H, 6.49.

Workup

  1. filtrationwas filtered
  2. customto remove unreacted magnesium
  3. washThe filtrate was washed with a saturated NH4Cl aqueous solution, water, and brine
  4. dry with materialwas dried over anhydrous MgSO4
  5. customAfter removal of the solvents under reduced pressure
  6. customthe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-ec42bb2718994e0eba953d8237266602
Source dataset
uspto-grants-2011_06
Patent number
US07960571B2

Reaction notes

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