Carbamate → HCID 66628868, compound

HRID 1021092Notes

Reaction equation

[CH2:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:2]#[CH:3].[C:10](=[O:13])([O-:12])[NH2:11]>>[C:4]1([CH2:1][C:2]#[C:3][C:6]2[CH:5]=[C:4]([CH2:1][CH2:2][CH2:3][NH:11][C:10](=[O:12])[O:13][C:4]([CH3:9])([CH3:5])[CH3:1])[CH:9]=[CH:8][CH:7]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

Reactant 2

HCID 276Carbamate

HCID 575753Benzylacetylene

Product 1

HCID 66628868HCID 66628868, compound

Procedure

Coupling of prop-2-ynylbenzene with bromide 57 was conducted following the method used in Example 22. Purification by flash chromatography (6% EtOAc-hexanes) gave tert-butyl 3-(3-(3-phenylprop-1-ynyl)phenyl)propylcarbamate as a brown oil. Yield (0.85 g, 73%): 1H NMR (400 MHz, CDCl3) δ 7.41-7.43 (m, 2H), 7.35 (t, J=8.0 Hz, 2H), 7.10-7.28 (m, 5H), 4.52 (br s, 1H), 3.84 (s, 2H), 3.14-3.16 (m, 2H), 2.61 (t, J=7.6 Hz, 2H), 1.80 (quint, J=7.6 Hz, 2H), 1.48 (s, 9H).

Workup

customPurification by flash chromatography (6% EtOAc-hexanes)

Sources & evidence

ORD record: ord-707ce3efabd64b9c82b9c74b124b2445
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08716529B2

Reaction notes

Loading…