1,7-Octadiyne → 2-(Dodeca-5,11-diynyloxy)tetrahydropyran

HRID 918971Notes

Reaction equation

HRID 918971 reaction equation
C#CCCCCC#C.BrCCCCOC1CCCCO1.[CH2:21]([O:36][CH:37]1[CH2:42][CH2:41][CH2:40][CH2:39][O:38]1)[CH2:22][CH2:23][CH2:24][C:25]#[C:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]CC#C>>[CH2:21]([O:36][CH:37]1[CH2:42][CH2:41][CH2:40][CH2:39][O:38]1)[CH2:22][CH2:23][CH2:24][C:25]#[C:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]#[CH:32]

Participants

4

Reactant 3

HCID 700991,7-OctadiyneHCID 5590192-(4-Bromobutoxy)tetrahydro-2H-pyranHCID 866652612-(Pentadeca-5,14-diynyloxy)tetrahydropyran

Product 1

HCID 121135252-(Dodeca-5,11-diynyloxy)tetrahydropyranYield 65%

Procedure

Oct-1,7-diyne (9.0 g, 84.9 mmol; G F Smith) was alkylated with 2-(4-bromobutoxy)-tetrahydropyran (15 g, 63.68 mmol) as described above for the synthesis of 2-(pentadeca-5,14-diynyloxy)tetrahydropyran to give 2-(dodeca-5,11-diynyloxy)tetrahydropyran (10.85 g, 65%) as a colorless oil. TLC: 10% EtOAc/hexanes, Rf≈0.6; 1H NMR (400 MHz, CDCl3) δ 4.57 (t, J=2.5 Hz, 1H), 3.82-3.87 (m, 1H), 3.70-3.77 (m, 1H), 3.46-3.51 (m, 1H), 3.36-3.42 (m, 1H), 2.14-2.20 (m, 6H), 1.93 (t, 1H, J=2.5 Hz), 1.46-1.72 (m, 14 H).

Sources & evidence

ORD record
ord-eec32ce54bf94cb982ca1112c5d8f95b
Source dataset
uspto-grants-2016_03
Patent number
US09272991B2

Reaction notes

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