1-Bromododecane → 2-(pentadec-2-ynyloxy)tetrahydro-2H-pyran

HRID 918985Notes

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][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>>[CH2:1]([O:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][O:6]1)[C:2]#[C:3][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH3:12]

Participants

Reactant 2

HCID 89191-Bromododecane

HCID 98609Tetrahydro-2-(2-propynyloxy)-2H-pyran

Product 1

HCID 674233292-(pentadec-2-ynyloxy)tetrahydro-2H-pyranYield 80%

Procedure

Alkylation of 2-(prop-2-ynyloxy)tetrahydro-2H-pyran (15.5 g, 110.71 mmol) with 1-bromododecane (34.0 g, 132.04 mmol) as described above gave 2-(pentadec-2-ynyloxy)tetrahydro-2H-pyran (27.2 g, 80%) which was used without further purification. TLC: 10% EtOAc/hexanes, Rf≈0.5.

Sources & evidence

ORD record: ord-a16f454496e0484e9bebc993c6bf8143
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09272991B2

Reaction notes

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