Triphenylphosphine → HCID 54578471, compound

HRID 2171211Notes

Reaction equation

[OH:1][CH2:2][C:3]([CH3:9])([CH3:8])[C:4]([O:6][CH3:7])=[O:5].CCOC(/N=N/C(OCC)=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[C:42]1[C:47]([O:48][CH3:49])=[C:46]([O:50][CH3:51])[CH:45]=[CH:44][C:43]=1[C:52]1[CH:53]=[C:54]2[C:58](=[CH:59][CH:60]=1)[C:57](=[O:61])[O:56][CH2:55]2>O1CCCC1.C(OCC)(=O)C>[CH3:49][O:48][C:47]1[C:46]([O:50][CH3:51])=[CH:45][CH:44]=[C:43]([C:52]2[CH:53]=[C:54]3[C:58](=[CH:59][CH:60]=2)[C:57](=[O:61])[O:56][CH2:55]3)[C:42]=1[O:1][CH2:2][C:3]([CH3:9])([CH3:8])[C:4]([O:6][CH3:7])=[O:5]

Participants

Conditions

Temperature: 70 °C

Procedure

To a stirring solution of methyl 3-hydroxy-2,2-dimethylpropanoate (2.76 g, 20.94 mmol, in portions) in tetrahydrofuran (25 mL) was added diethylazodicarboxylate (2.43 g, 13.96 mmol), triphenylphosphine (3.59 g, 13.96 mmol) and 5-(2-hydroxy-3,4-dimethoxyphenyl)isobenzofuran-1(3H)-one (2 g, 6.98 mmol) and the resultant reaction mixture was heated to 70° C. for 6 h. The reaction mixture was diluted with ethyl acetate layer, washed with water, dried over anhydrous sodium sulphate and concentrated under reduced pressure. Purification of the residue by flash, column chromatography (silica gel, 0-20% ethyl acetate in pet ether) to afford the title compound as a solid (800 mg, 28.6%).

Workup

customthe resultant reaction mixture
washwashed with water
dry with materialdried over anhydrous sodium sulphate
concentrationconcentrated under reduced pressure
customPurification of the residue by flash, column chromatography (silica gel, 0-20% ethyl acetate in pet ether)

Sources & evidence

ORD record: ord-688c09b5c85d441985d31e9895dbfe17
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09051290B2

Reaction notes

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