1,10-Phenanthroline → 4-(trans-But-2-enyloxy)anisole

HRID 2179254Notes

Reaction equation

N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C([O-])([O-])=O.[Cs+].[Cs+].I[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1.[CH2:30]([OH:34])/[CH:31]=[CH:32]/[CH3:33]>[Cu]I.C1(C)C=CC=CC=1>[CH2:30]([O:34][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)/[CH:31]=[CH:32]/[CH3:33]

Participants

Conditions

Temperature: 110 °C

Procedure

A test tube was charged with CuI (20 mg, 0.10 mmol, 0.10 equiv), 1,10-phenanthroline (36 mg, 0.20 mmol, 0.20 equiv), Cs2CO3 (652 mg, 2.0 mmol, 2.0 equiv), 4-iodoanisole (234 mg, 1.0 mmol, 1.0 equiv), trans-2-buten-1-ol (171 μL, 2.0 mmol, 2.0 equiv) and toluene (0.5 mL). The test tube was sealed and the reaction mixture was stirred at 110° C. for 22 h. The resulting suspension was cooled to room temperature and filtered through a 0.5×1 cm pad of silica gel, eluting with diethyl ether. The filtrate was concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (2×20 cm; pentane:diethyl ether 30:1) provided 153 mg (86% yield) of the title compound as a light yellow oil.

Workup

customThe test tube was sealed
temperatureThe resulting suspension was cooled to room temperature
filtrationfiltered through a 0.5×1 cm pad of silica gel
washeluting with diethyl ether
concentrationThe filtrate was concentrated in vacuo
customPurification of the residue by flash chromatography on silica gel (2×20 cm; pentane:diethyl ether 30:1)

Sources & evidence

ORD record: ord-3cd346940fac4f72afaa1174370900fb
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067955B2

Reaction notes

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