Allyl Alcohol → HCID 19390567, compound

HRID 1756506Notes

Reaction equation

HRID 1756506 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:14]([O-:16])=[O:15])[CH:10]=2)[N:5]=1)([OH:3])=[O:2].[C:17]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:22]=CC=C[CH:18]=1.C(O)C=C.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH2:22]([O:2][C:1]([C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:14]([O-:16])=[O:15])[CH:10]=2)[N:5]=1)=[O:3])[CH:17]=[CH2:18]

Participants

6

Reactant 4

HCID 7858Allyl AlcoholHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 123242586-Nitroquinoline-2-carboxylic acid

Product 1

HCID 19390567HCID 19390567, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-carboxy-6-nitroquinoline (1.5 g; 6.8 mM) in THF (30 ml) was added triphenylphosphine (2.7 g; 10.2 mM), allyl alcohol (0.7 ml; 10.2 mM) and DEAD (1.63 ml; 10.2 mM). After stirring at ambient temperature for 30 minutes, the mixture was extracted with ethyl acetate and purified by subjecting to flash chromatography, eluting with ethyl acetate/petroleum ether (40/60) to give 2-allyloxycarbonyl-6-nitroquinoline (1.2 g; 71%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. custompurified
  3. washeluting with ethyl acetate/petroleum ether (40/60)

Sources & evidence

ORD record
ord-4829ac0a5a7a47a0a393574887d40ef1
Source dataset
uspto-grants-1995_08
Patent number
US05441949

Reaction notes

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