Tetrahydrofuran → HCID 11989419, compound

HRID 2423268Notes

Reaction equation

HRID 2423268 reaction equation
[CH3:1][C:2]([CH3:6])=[CH:3][Mg]Br.O1CC[CH2:9][SiH2:8]1.[CH3:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].C([O:21][CH2:22]C)(=O)C.[CH2:24]1COCC1>C(OCC)C>[OH:21][CH2:22][C:14]1[CH:13]=[CH:12][CH:17]=[CH:16][C:15]=1[Si:8]([CH3:9])([CH3:24])[CH:3]=[C:2]([CH3:6])[CH3:1]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 21226206Ethyl acetate hexaneHCID 123209143HCID 123209143, compoundHCID 178448304HCID 178448304, compound

Product 1

HCID 11989419HCID 11989419, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

At 0° C., a 0.5 M THF solution of 2-methyl-1-propenylmagnesium bromide (100 mL, 50 mmol) was added to a solution of oxasilacyclopentane (7) (7.5 g, 46 mmol) in THF (50 mL), and the resulting mixture was stirred at room temperature overnight and then was diluted with diethyl ether. The resulting mixture was washed with a saturated NH4Cl aqueous solution, water, and brine, and then was dried over anhydrous MgSO4. The solvent was removed under reduced pressure, and the residue was purified by flash chromatography on neutral aluminum oxide (activity grade III), thereby obtaining (2-(hydroxymethyl)phenyl)dimethyl(2-methyl-1-propenyl)silane: 1g (7.1 g, yield of 71%) as a colorless oil, Rf: 0.26 (hexane-ethyl acetate=5:1). 1H NMR (400 MHz, C6D6) δ 7.57 (d, J=7.3 Hz, 1H), 7.45 (d, J=7.7 Hz, 1H), 7.22 (dd, J=7.4, 7.3 Hz, 1H), 7.13 (dd, J=7.7, 7.4 Hz, 1H), 5.41 (s, 1H), 4.63 (d, J=5.9 Hz, 2H), 1.78 (t, J=5.9 Hz, 1H), 1.66 (s, 3H), 1.46 (s, 3H), 0.37 (s, 6H); 13C NMR (101 MHz, C6D6) δ 153.4, 147.3, 137.5, 134.9, 129.7, 128.0, 127.0, 123.8, 65.3, 29.3, 23.2, 0.0; Anal. Calcd for C13H20Osi; C, 70.85; H, 9.15. Found: C, 70.83; H, 9.23.

Workup

  1. washThe resulting mixture was washed with a saturated NH4Cl aqueous solution, water, and brine
  2. dry with materialwas dried over anhydrous MgSO4
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified by flash chromatography on neutral aluminum oxide (activity grade III)

Sources & evidence

ORD record
ord-116969a8e039416f9cb812a58d778354
Source dataset
uspto-grants-2011_06
Patent number
US07960571B2

Reaction notes

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