2,6-Dichlorophenol → HCID 86731079, compound

HRID 1844407Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[OH:9].O[CH2:11][CH2:12][C@H:13]([N:15]1[C:23](=[O:24])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]1=[O:25])[CH3:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1.C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[O:9][CH2:11][CH2:12][C@H:13]([N:15]1[C:23](=[O:24])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]1=[O:25])[CH3:14]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2,6-dichlorophenol (14.9 mg, 0.091 mmol) in THF (1.5 mL) was added (R)-2-(4-hydroxybutan-2-yl)isoindoline-1,3-dione (20 mg, 0.091 mmol) and triphenylphosphine (47.9 mg, 0.182 mmol) and the reaction mixture was cooled to 0° C. in an ice/water bath. DIAD (0.035 mL, 0.182 mmol) was added drop wise and the reaction mixture was stirred at 0° C. for 1 h. The reaction mixture was allowed to warm to rt and was stirred at rt overnight. The reaction mixture was concentrated under vacuum to yield a yellow oil that was diluted with a minimal amount of DCM, loaded onto a 12 g ISCO column and purified by ISCO. Intermediate 13A (0.1003 g, 96% yield) was isolated as a clear oil. LC-MS (ESI) 365 (M+H), RT=2.84 min (Method A). NMR indicated that the final product contained reduced DIAD.

Workup

temperatureto warm to rt
stirringwas stirred at rt overnight
concentrationThe reaction mixture was concentrated under vacuum
customto yield a yellow oil that
custompurified by ISCO

Sources & evidence

ORD record: ord-7743de142add457181450d36d711748a
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946430B2

Reaction notes

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