HCID 572998, compound → HCID 86607017, compound

HRID 970031Notes

Reaction equation

[CH2:1]([O:3][C@@H:4]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][OH:19])=[CH:13][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:2].[CH3:20][S:21]([O:24][C:25]1[CH:30]=[CH:29][C:28](O)=[CH:27][CH:26]=1)(=[O:23])=[O:22]>C1COCC1>[CH2:1]([O:3][C@@H:4]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:17][CH2:18][O:19][C:28]2[CH:27]=[CH:26][C:25]([O:24][S:21]([CH3:20])(=[O:22])=[O:23])=[CH:30][CH:29]=2)=[CH:15][CH:16]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:2]

Participants

Conditions

Temperature: 150 °C

Procedure

A solution of cyanomethylenetri-N-butylphosphorane (0.663 g, 2.75 mmol) in THF (1.5 mL) was added to a solution of ethyl(2S)-2-ethoxy-3-[4-(2-hydroxyethyl)phenyl]-propanoate (0.244 g, 0.92 mmol) and 4-hydroxyphenyl methanesulfonate (0.172 g, 0.92 mmol) in THF (1.5 mL). The reaction mixture was heated at 150° C. in a microwave oven for 10 minutes. The solvent was removed under reduced pressure. The crude product was purified by flash chromatography (silica, heptane/ethyl acetate 3:1 as the mobile phase) affording 0.167 g (42%) of the title compound.

Workup

customThe solvent was removed under reduced pressure
customThe crude product was purified by flash chromatography (silica, heptane/ethyl acetate 3:1 as the mobile phase)

Sources & evidence

ORD record: ord-abf2507a4e7344e9bb848495e4cbab10
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07309720B2

Reaction notes

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