2,6-Dichlorophenol → HCID 86731079, compound

HRID 1053678Notes

Reaction equation

HRID 1053678 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>[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

6

Reactant 4

HCID 68992,6-DichlorophenolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 11127767HCID 11127767, compound

Product 1

HCID 86731079HCID 86731079, compoundYield 301.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2,6-dichlorophenol (14.9 mg, 0.0910 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, 0.18 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 stirred at rt for 16 h. The reaction mixture was concentrated under vacuum to yield a yellow oil that was purified by flash chromatography. Intermediate 8A (0.10 g, 96% yield) was isolated as a clear oil. LC-MS (ESI) 365 (M+H), RT=2.84 min (Method A).

Workup

  1. temperatureto warm to rt
  2. stirringstirred at rt for 16 h
  3. concentrationThe reaction mixture was concentrated under vacuum
  4. customto yield a yellow oil that
  5. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-c2f863689e314454a35b85dce550d871
Source dataset
uspto-grants-2016_07
Patent number
US09394260B2

Reaction notes

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