4-Hydroxybenzaldehyde → HCID 11623284, compound

HRID 1383938Notes

Reaction equation

HRID 1383938 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH3:12])[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].O[C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1C=CC=CC=1>[CH:18]([C:17]1[CH:20]=[CH:21][C:14]([O:1][CH2:2][CH2:3][N:4]([CH3:12])[C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])=[CH:15][CH:16]=1)=[O:19]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 545700N-(tert-Butoxycarbonyl)-N-methyl-2-aminoethanol

Product 1

HCID 11623284HCID 11623284, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of N-(2-hydroxyethyl)-N-methylcarbamic acid, 1,1-dimethylethyl ester (7.05 g, 40.2 mmol; W. S. Saari and all, J. Med. Chem. 33, 97 (1990)), 4-hydroxybenzaldehyde (3.75 g, 30.7 mmol) and triphenylphosphine (10.57 g, 40.3 mmol) in dry benzene (120 ml) was cooled to 15° C. and treated with diisopropyl azodicarboxylate (8.15 g, 40.3 mmol) in dry benzene (20 ml) added dropwise over 20 min. After 16 h at 22° C., and chromatography on silica gel (elution toluene-ethyl acetate 9:1-8:2) gave 4.40 g (52%) of the title material as white cubes: mp 62-65° C. (ether-hexane).

Workup

  1. additionadded dropwise over 20 min

Sources & evidence

ORD record
ord-13c60cdfbfe64bc5b92982992aecd355
Source dataset
uspto-grants-2001_07
Patent number
US06255496B1

Reaction notes

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