p-Toluenesulfonic acid → 3-(4-Allyldimethylsilylphenyl)-1-propanol

HRID 2228392Notes

Reaction equation

HRID 2228392 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][O:13]C2CCCCO2)=[C:6]([SiH:20]([CH3:22])[CH3:21])[CH:5]=1)[CH:2]=[CH2:3].CC1C=CC(S(O)(=O)=O)=CC=1>CO>[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][OH:13])=[C:6]([SiH:20]([CH3:22])[CH3:21])[CH:5]=1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 1317233832-[3-(4-Allyldimethylsilylphenyl)propoxy]tetrahydro-2H-pyran

Product 1

HCID 1317233843-(4-Allyldimethylsilylphenyl)-1-propanolYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-[3-(4-allyldimethylsilylphenyl)propoxy]tetrahydro-2H-pyran (3 Scheme 22, 600 mg, 1.9 mmol) was treated with catalytic amount of p-TsOH (20 mg) in methanol (10 mL). After being stirred for 16 h at room temperature, the reaction mixture was concentrated under reduced pressure and purified by column chromatography (1:5 ethyl acetate/hexanes) to afford a colorless oil (342 mg, 77%); 1H NMR (300 MHz, CDCl3) δ 0.31 (s, 6 H), 1.79 (d, J=8.1 Hz, 2 H), 1.93 (m, 2 H), 2.74 (t, J=8.4 Hz, 2 H), 3.71 (d, J=6.6 Hz, 2 H), 4.87 (s, 1 H), 4.92 (m, 1 H), 5.81 (m, 1 H), 7.24 (d, J=7.8 2 H), 7.50 (d, J=7.8 Hz, 2 H); 13C NMR (75 MHz, CDCl3) −3.1, 24.1, 32.4, 34.4, 62.4, 113.6, 128.2, 133.9, 135.0, 135.9, 143.1; HRMS (EI) calcd for C14H22OSi 234.1439, found 234.1440.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. custompurified by column chromatography (1:5 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-2c6f9801df2049719a3430a761bcc7dd
Source dataset
uspto-grants-2002_07
Patent number
US06416861B1

Reaction notes

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