Triphenylphosphine → HCID 66737532, compound

HRID 1640528Notes

Reaction equation

HRID 1640528 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[OH:13].[CH3:14][C:15]1([CH3:25])[O:19][C@H:18]([CH2:20]/[CH:21]=[CH:22]/[CH2:23]O)[CH2:17][O:16]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH3:14][C:15]1([CH3:25])[O:19][C@H:18]([CH2:20][CH:21]=[CH:22][CH2:23][O:13][C:6]2[C:5]3[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=3)[N:9]=[CH:8][CH:7]=2)[CH2:17][O:16]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 66737199HCID 66737199, compoundHCID 178487890HCID 178487890, compound

Product 1

HCID 66737532HCID 66737532, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6-methoxy-quinolin-4-ol (0.54 g, 3 mmol) and (E)-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-but-2-en-1-ol (prepared according to J. Am. Chem. Soc. (2001), 123, 9525; 0.53 g, 3 mmol) in THF was treated with PPh3 (977 mg, 1.2 eq.) and dropwise with DIAD (0.77 mL, 1.2 eq.). The mixture was stirred at rt for 3 days, concentrated in vacuo and purified by FC (EA) to give the product as a yellowish oil (0.73 g, 72% yield).

Workup

  1. concentrationconcentrated in vacuo
  2. custompurified by FC (EA)

Sources & evidence

ORD record
ord-25c7acc7f40e449388aa941a980b0df0
Source dataset
uspto-grants-2012_02
Patent number
US08114867B2

Reaction notes

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