Selective Deprotection of tert-Butyldimethylsilyl Ethers Using Nafion-H®/Sodium Iodide (or Bromodimethylsulfonium Bromide) in Methanol

References

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• Spectral data of alcohol corresponding to Entry 16. IR (neat) νmax: 3355 cm−1. 1H NMR (CDCl3 400 MHz): δ 0.00 (s, 6H, Si(CH 3)2), 0.79 (s, 9H, SiC(CH 3)3), 3.17 (s, 1H, ArCH2OH), 4.19–4.40 (m, 2H, ArCH 2OH), 6.56–7.07 (m, 4H, C6 H 4<). 13C NMR (100 MHz): δ −4.46, 25.66, 57.70, 65.09, 74.41, 115.26, 120.17, 128.61, 129.69, 133.49, 155.31, 155.58. Analysis calcd. for C13H22O2Si: C, 65.5; H, 9.30%. Found: C, 65.48; H, 9.33%. Spectral data of alcohol corresponding to Entry 17. IR (neat) νmax: 3311 cm−1. 1H NMR (CDCl3 400 MHz): δ 0.19 (s, 3H, SiCH 3), 0.26 (s, 3H, SiCH 3), 0.97 (s, 9H, SiC(CH 3)3), 1.02 (s, 9H, SiC(CH 3)3), 3.42 (s, 1H, ArCH2OH), 4.58 (s, 2H, ArCH 2OH), 6.33–7.13 (m, 4H, C6 H 4<). 13C NMR (100 MHz): δ −4.47, −4.42, −4.22, 18.14, 18.22, 25.66, 25.70, 29.69, 61.67, 69.88, 110.80, 113.05, 124.50, 129.69, 154.36, 156.11, 156.73. Analysis calcd. for C19H36O3Si2: C, 61.90; H, 9.84%. Found: C, 61.93; H, 9.81%
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