1,3-Dibromopropane → HCID 59272425, compound

HRID 1875365Notes

Reaction equation

[CH3:1][C:2]([C:4]1[C:9]([OH:10])=[C:8]([O:11][CH3:12])[C:7]2[O:13][CH:14]=[CH:15][C:6]=2[C:5]=1[O:16][CH3:17])=[O:3].C([O-])([O-])=O.[K+].[K+].[Br:24][CH2:25][CH2:26][CH2:27]Br>>[C:2]([C:4]1[C:9]([O:10][CH2:27][CH2:26][CH2:25][Br:24])=[C:8]([O:11][CH3:12])[C:7]2[O:13][CH:14]=[CH:15][C:6]=2[C:5]=1[O:16][CH3:17])(=[O:3])[CH3:1]

Participants

Reactant 3

HCID 80011,3-Dibromopropane

HCID 11430Potassium Carbonate

HCID 68086Khellinone

Product 1

HCID 59272425HCID 59272425, compoundYield 88%

Procedure

Khellinone (400 mg, 1.7 mmol, 0.3 M), K2CO3 (3 eqs) and 1,3-dibromopropane (3 eqs) were reacted according to General Procedure A. The crude product was purified by flash chromatography, eluting with ethyl acetate:petroleum ether (15:85) to afford the title compound as a clear oil (530 mg, 88%). 1H NMR (300 MHz, CDCl3): δ 2.24 (quintet, J=6.2 Hz, 2H), 2.51 (s, 3H), 3.57 (t, J=6.6 Hz, 2H), 3.97 (s, 3H), 4.07 (s, 3H), 4.19 (t, J=6.4 Hz, 2H), 6.86 (d, J=2.2 Hz, 1H), 7.56 (d, J=2.2 Hz, 1H). MS (ES+) m/z 356.8/358.8 (M+H+).

Workup

customThe crude product was purified by flash chromatography
washeluting with ethyl acetate:petroleum ether (15:85)

Sources & evidence

ORD record: ord-939b0512fdab43079c5e02fb679078c1
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309545B2

Reaction notes

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