Tetrahydro-2-(2-propynyloxy)-2H-pyran → tert-butyldiphenyl(7-(tetrahydro-2H-pyran-2-yloxy)hept-5-ynyloxy)silane

HRID 918982Notes

Reaction equation

HRID 918982 reaction equation
[CH2:1]([O:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][O:6]1)[C:2]#[CH:3].Br[CH2:12][CH2:13][CH2:14][CH2:15][O:16][Si:17]([C:30]([CH3:33])([CH3:32])[CH3:31])([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[C:30]([Si:17]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[O:16][CH2:15][CH2:14][CH2:13][CH2:12][C:3]#[C:2][CH2:1][O:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][O:6]1)([CH3:31])([CH3:32])[CH3:33]

Participants

3

Reactant 2

HCID 98609Tetrahydro-2-(2-propynyloxy)-2H-pyranHCID 14362384(4-Bromobutoxy)(tert-butyl)diphenylsilane

Product 1

HCID 67424106tert-butyldiphenyl(7-(tetrahydro-2H-pyran-2-yloxy)hept-5-ynyloxy)silaneYield 65%

Procedure

2-(Prop-2-ynyloxy)tetrahydro-2H-pyran (5.6 g, 36.36 mmol) was alkylated with (4-bromobutoxy)(tert-butyl)diphenylsilane (18.5 g, 47.2 mmol) as described above to give tert-butyldiphenyl(7-(tetrahydro-2H-pyran-2-yloxy)hept-5-ynyloxy)silane (10.64 g, 65%) and used after extractive isolation without further purification. TLC: 10% EtOAc/hexanes, Rf≈0.5.

Sources & evidence

ORD record
ord-08acd38438e94696a481f557552f2b32
Source dataset
uspto-grants-2016_03
Patent number
US09272991B2

Reaction notes

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