Tetrahydrofuran → HCID 68887960, compound

HRID 1819550Notes

Reaction equation

[Mg].[CH2:2]([O:9][C:10]1[C:19](=[O:20])[C:18]2[C:13](=[CH:14][C:15](I)=[CH:16][CH:17]=2)[O:12][C:11]=1[C:22]1[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[C:24]([O:32][CH3:33])[CH:23]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.O1[CH2:38][CH2:37][CH2:36][CH2:35]1>[Cl-].[Zn+2].[Cl-]>[CH2:2]([O:9][C:10]1[C:19](=[O:20])[C:18]2[C:13](=[CH:14][C:15]([CH2:35][CH2:36][CH:37]([CH3:38])[CH2:15][CH2:16][CH2:17][CH:18]([CH3:13])[CH2:19][CH2:10][CH2:11][CH:22]([CH3:27])[CH3:23])=[CH:16][CH:17]=2)[O:12][C:11]=1[C:22]1[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[C:24]([O:32][CH3:33])[CH:23]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirring suspension of zinc chloride (0.367 g, 2.7 mmol, 3 eq) and magnesium (0.100 g, 4.1 mmol, 4.7 eq) in tetrahydrofuran (2.5 ml) under argon was added 7 (1.268 g, 3.8 mmol, 4.2 eq) in tetrahydrofuran (2.5 ml). The reaction was heated to 50° C. for 19 hours then cooled. 34 (0.481 g, 0.8 mmol) in tetrahydrofuran (7 ml) and dichlorobis-[tri-(o-tolyl)-phosphinyl]palladium (0.063 g, 0.08 mmol, 0.09 eq) added and the reaction stirred for 25 hours. The reaction was then quenched with 3 N HCl (10 ml), diluted with water and extracted into ethyl acetate (3×). The combined aqueous layers were dried (MgSO4) and concentrated in vacuo to give a purple oil. Column chromatography (silica gel, petrol:EtOAc 9:1>2:1) yielded 48 (0.082 g, 15%) as a pale yellow oil.

Workup

temperaturethen cooled
customThe reaction was then quenched with 3 N HCl (10 ml)
additiondiluted with water
extractionextracted into ethyl acetate (3×)
dry with materialThe combined aqueous layers were dried (MgSO4)
concentrationconcentrated in vacuo
customto give a purple oil

Sources & evidence

ORD record: ord-4f7c50951f18419cb3aaa3bbe53123d1
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601754B2

Reaction notes

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