Benzyl Alcohol → HCID 178439763, compound

HRID 522367Notes

Reaction equation

HRID 522367 reaction equation
[CH2:1]([C:4]1[C:5]([OH:15])=[N:6][C:7]2[C:12]([C:13]=1[OH:14])=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:2]=[CH2:3].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:35](O)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1.C(Cl)Cl.C(OCC)C>[CH2:35]([O:14][C:13]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5]([OH:15])[C:4]=1[CH2:1][CH:2]=[CH2:3])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

8

Reactant 4

HCID 244Benzyl AlcoholHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 178439761HCID 178439761, compound

Product 1

HCID 178439763HCID 178439763, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 3-(prop-2-en-1-yl)quinoline-2,4-diol (4.0 g), triphenylphosphine (6.78 g) and benzyl alcohol (2.27 ml) in THF (240 ml) at 0° C. was added dropwise a THF (12 mL) solution of diisopropylazodicarboxylate (5.02 ml). Upon completion of addition, the mixture was allowed to stir at room temperature for 60 minutes. The reaction mixture was concentrated in vacuo to give a thick oil. Oil dissolved in DCM (20 mL) and solids started to precipitate. The solids were filtered and washed with DCM (10 mL). This provided 2.0 g of the desired product. Purification of the mother liquors using flash chromatography (ISCO, 1-8% acetone/DCM) gave an oil that was a mixture of products. This oil was dissolved in 15 mL of diethyl ether and seeded with the desired product. The mixture was stirred overnight and crystallization occurred. The solids were filtered and washed with ether to provide the desired product (1.06 g) as a white solid for a total of 3.06 g of product. LRMS (ES+) M/Z (M+H)+ 292.1.

Workup

  1. additionUpon completion of addition
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customto give a thick oil
  4. customto precipitate
  5. filtrationThe solids were filtered
  6. washwashed with DCM (10 mL)
  7. customPurification of the mother liquors
  8. customgave an oil that
  9. additiona mixture of products

Sources & evidence

ORD record
ord-5067a4fd1aed4d7e8750b8ff422dac91
Source dataset
uspto-grants-2016_05
Patent number
US09328138B2

Reaction notes

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