Phenylacetaldehyde → HCID 67385401, compound

HRID 1471921Notes

Reaction equation

HRID 1471921 reaction equation
[C:1]1([CH2:7][CH:8]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH3:20][O:21][CH2:22][CH2:23][C:24](Cl)=O.O.[NH2:28][NH2:29]>C1(C)C=CC=CC=1.C(O)C>[CH3:20][O:21][CH2:22][CH2:23][C:24]1[NH:29][N:28]=[CH:8][C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 998PhenylacetaldehydeHCID 24654Hydrazine hydrate (1:1)HCID 2733832Lithium HexamethyldisilazideHCID 27597283-Methoxypropanoyl chloride

Product 1

HCID 67385401HCID 67385401, compoundYield 37.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

To a solution of 2-phenylacetaldehyde (4.0 g, 33.3 mmol) in toluene (10 mL), were added LiHMDS (33.3 mL, 33.3 mmol) at 0° C. After stirring for 10 min, 3-methoxypropanoyl chloride (4.08 g, 33.3 mmol) was added and continued stirring for 30 min at 0° C. The reaction was quenched with acetic acid (glacial, 2 mL), diluted with ethanol (75 mL), and hydrazine hydrate (5.00 g, 100 mmol) was added. The reaction was brought to reflux for 4 hrs. After cooling to room temperature, the reaction was concentrated and extracted with EtOAc, dried over MgSO4, and purified by column chromatography to give the title compound as yellowish oil (2.5 g). LCMS m/z 203.1 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 2.85 (t, J=6.69 Hz, 2H), 3.17 (s, 3H), 3.48 (t, J=6.63 Hz, 2H), 5.75 (s, 1H), 7.31-7.38 (m, 3H), 7.41-7.47 (m, 2H), 13.08 (s, 1H).

Workup

  1. stirringcontinued stirring for 30 min at 0° C
  2. customThe reaction was quenched with acetic acid (glacial, 2 mL)
  3. additionwas added
  4. temperatureto reflux for 4 hrs
  5. concentrationthe reaction was concentrated
  6. extractionextracted with EtOAc
  7. dry with materialdried over MgSO4
  8. custompurified by column chromatography

Sources & evidence

ORD record
ord-e16e9d36a9d94b118b6721f98968f34b
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

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