tert-butyldiphenyl(7-(tetrahydro-2H-pyran-2-yloxy)hept-5-ynyloxy)silane → 7-(Tert-butyldiphenylsilyloxy)hept-2-yn-1-ol

HRID 918983Notes

Reaction equation

HRID 918983 reaction equation
[C:1]([Si:5]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[O:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]#[C:12][CH2:13][O:14]C1CCCCO1)([CH3:4])([CH3:3])[CH3:2]>CCOCC>[Si:5]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]#[C:12][CH2:13][OH:14])([C:1]([CH3:3])([CH3:4])[CH3:2])([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

3

Reactant 1

HCID 67424106tert-butyldiphenyl(7-(tetrahydro-2H-pyran-2-yloxy)hept-5-ynyloxy)silane

Product 1

HCID 143623857-(Tert-butyldiphenylsilyloxy)hept-2-yn-1-olYield 88%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Removal of the THP ether from tert-butyldiphenyl(7-(tetrahydro-2H-pyran-2-yloxy)hept-5-ynyloxy)silane (10 g, 22.22 mmol) as described above furnished 7-(tert-butyldiphenylsilyloxy)hept-2-yn-1-ol (7.15 g, 88%) as a colorless oil. TLC: 30% EtOAc/hexanes, Rf≈0.40; 1H NMR (CDCl3, 300 MHz) δ 7.65-7.67 (m, 4H), 7.33-7.42 (m, 6H), 4.22-4.26 (m, 2H), 3.64 (t, 2H, J=6.4 Hz), 2.12-2.16 (m, 2H), 1.40-1.46 (m, 4H), 1.03 (s, 9H).

Sources & evidence

ORD record
ord-df289d798c374d65a08faf93f80c9216
Source dataset
uspto-grants-2016_03
Patent number
US09272991B2

Reaction notes

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