1-Methoxy-2-propanol → HCID 70982964, compound

HRID 338926Notes

Reaction equation

HRID 338926 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([OH:12])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O.[CH3:44][O:45][CH2:46][CH:47](O)[CH3:48]>C1COCC1.O>[CH3:44][O:45][CH2:46][CH:47]([O:12][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[N:3]=[C:2]([CH3:1])[CH:11]=[CH:10]2)[CH3:48]

Participants

7

Reactant 4

HCID 79001-Methoxy-2-propanolHCID 11776TriphenylphosphineHCID 132242-Methyl-8-hydroxyquinolineHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 70982964HCID 70982964, compoundYield 68.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 2-methylquinolin-8-ol (1.0 g, 6.28 mmol) in THF (5 mL) was added PPh3 (6.92 g, 26.4 mmol), DEAD (1.58 ml, 10.1 mmol) and 1-methoxypropan-2-ol (0.736 g, 8.17 mmol). The reaction was stirred for 24 hours at ambient temperature and then water was added. The aqueous phase was extracted with DCM and the combined organic phases dried over MgSO4, filtered and purified by reverse chromatography (SP4, 40M, eluting with a gradient of water/ACN 100:0 to 0:100, 20 column volumes) to yield 8-(1-methoxypropan-2-yloxy)-2-methylquinoline (1.0 g, 68.8% yield) as a clear liquid

Workup

  1. extractionThe aqueous phase was extracted with DCM
  2. dry with materialthe combined organic phases dried over MgSO4
  3. filtrationfiltered
  4. custompurified by reverse chromatography (SP4, 40M
  5. washeluting with a gradient of water/ACN 100:0 to 0:100, 20 column volumes)

Sources & evidence

ORD record
ord-edcdf05a56e4433f9d365bd4bb06e261
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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