2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → Methyl 7-(N-(4-(1-hydroxyhexyl)phenyl)acetamido)hept-5-ynoate

HRID 1015460Notes

Reaction equation

ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.COC1C=CC(C[O:22][CH:23]([C:29]2[CH:34]=[CH:33][C:32]([N:35]([CH2:39][C:40]#[C:41][CH2:42][CH2:43][CH2:44][C:45]([O:47][CH3:48])=[O:46])[C:36](=[O:38])[CH3:37])=[CH:31][CH:30]=2)[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=CC=1>C(Cl)(Cl)Cl.O>[OH:22][CH:23]([C:29]1[CH:30]=[CH:31][C:32]([N:35]([CH2:39][C:40]#[C:41][CH2:42][CH2:43][CH2:44][C:45]([O:47][CH3:48])=[O:46])[C:36](=[O:38])[CH3:37])=[CH:33][CH:34]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

Conditions

Temperature: 0 °C

Procedure

4,5-Dichloro-3,6-dioxo-1,4-cyclohexadiene-1,2-dicarbonitrile (19 mg, 0.081 mmol) was added to a solution of the MPM-ether 104 (35 mg, 0.071 mmol) in CHCl3 (1.6 mL) and H2O (0.1 mL) at 0° C. After stirring for 2 h at 0° C. the reaction was quenched with sodium bicarbonate and extracted with EtOAc. The organic portion was washed with saturated aqueous sodium hydrogen sulfate and brine, then dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, 3:2 hex/EtOAc) to yield 23 mg (87%) of the hydroxyl-ester 105.

Workup

customwas quenched with sodium bicarbonate
extractionextracted with EtOAc
washThe organic portion was washed with saturated aqueous sodium hydrogen sulfate and brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by flash column chromatography (silica gel, 3:2 hex/EtOAc)

Sources & evidence

ORD record: ord-1f26b48d92324fa997877b25511bf30c
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07985767B2

Reaction notes

Loading…