Triphenylphosphine → HCID 67266030, compound

HRID 1686149Notes

Reaction equation

HRID 1686149 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH:9]([O:12][CH3:13])[O:10][CH3:11])[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:34][CH2:35][N:36]([CH3:44])[C:37](=[O:43])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40].N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:34][CH2:35][N:36]([CH3:44])[C:37](=[O:43])[O:38][C:39]([CH3:41])([CH3:40])[CH3:42])=[C:4]([CH:9]([O:12][CH3:13])[O:10][CH3:11])[CH:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 545700N-(tert-Butoxycarbonyl)-N-methyl-2-aminoethanolHCID 21886104HCID 21886104, compound

Product 1

HCID 67266030HCID 67266030, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-bromo-2-dimethoxymethylphenol (6.00 g, 24.3 mmol) in benzene (100 ml) were added triphenylphosphine (7.63 g, 29.1 mmol) and t-butyl 2-hydroxyethylmethylcarbamate (5.10 g, 29.1 mmol) synthesized in step 1). The reaction solution was cooled to 0° C. in an ice bath, and diisopropyl azodicarboxylate (5.88 g. 5.73 ml, 29.1 mmol) was dropwise added thereto, after which it was allowed to react for 1 hour. Following extraction with brine and ethyl acetate, the organic layer was dried over anhydrous MgSO4 and filtered. The filtrate was concentrated in a vacuum. The residue was purified through column chromatography (ethyl acetate/n-hexane=1/20) to afford the object compound (colorless oil, 11.30 g, 96.1%).

Workup

  1. customto react for 1 hour
  2. extractionextraction with brine and ethyl acetate
  3. dry with materialthe organic layer was dried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in a vacuum
  6. customThe residue was purified through column chromatography (ethyl acetate/n-hexane=1/20)
  7. customto afford the object compound (colorless oil, 11.30 g, 96.1%)

Sources & evidence

ORD record
ord-2ae3f0c968dd4ca09ed8bc450e393398
Source dataset
uspto-grants-2012_04
Patent number
US08148541B2

Reaction notes

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