Methylparaben → HCID 18508138, compound

HRID 1356505Notes

Reaction equation

HRID 1356505 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.C[N:13]([CH3:18])[CH2:14][CH2:15]CO.C1(P([C:32]2[CH:37]=[CH:36]C=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=N[C:40](OC(C)C)=O>C1COCC1>[CH2:18]([N:13]([CH2:36][CH2:37][CH2:32][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1)[CH2:14][CH3:15])[CH3:40]

Participants

6

Reactant 4

HCID 7456MethylparabenHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 766463-(Dimethylamino)-1-propanol

Product 1

HCID 18508138HCID 18508138, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-hydroxybenzoate (1.0 g, 6.58 mmol), 3-dimethylamino-1-propanol (1.01 g, 9.87 mmol), and triphenylphosphine (2.6 g, 9.87 mmol) at 0° C. in THF (20 mL) was added dropwise diisopropyl azodicarboxylate (1.99 g, 9.87 mmol). After stirring for 16 h at room temperature the solution was concentrated and the residue purified by column chromatography (silica gel, methanol/dichloromethane) to yield the title compound as an oily solid (1.25 g, 5.2 mmol). MS(ESI): 238.1 (M+H)+.

Workup

  1. concentrationwas concentrated
  2. customthe residue purified by column chromatography (silica gel, methanol/dichloromethane)

Sources & evidence

ORD record
ord-1109b581503545c7bba658a38d98cf3c
Source dataset
uspto-grants-2003_07
Patent number
US06586466B2

Reaction notes

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