Formaldehyde → HCID 68494000, compound

HRID 1944198Notes

Reaction equation

HRID 1944198 reaction equation
C=O.[CH2:3]([O:10][C:11]1[CH:12]=[C:13]([CH2:19][CH:20]([NH:22][C:23](=[O:25])[CH3:24])[CH3:21])[CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O.[C:27](OCC)(=O)C>C1(C)C=CC=CC=1.CC1C=CC(S(O)(=O)=O)=CC=1>[CH2:3]([O:10][C:11]1[CH:12]=[C:13]2[C:14](=[CH:15][C:16]=1[O:17][CH3:18])[CH2:27][N:22]([C:23](=[O:25])[CH3:24])[CH:20]([CH3:21])[CH2:19]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 712Formaldehyde3×HCID 962WaterHCID 8857Ethyl AcetateHCID 68496071HCID 68496071, compound

Product 1

HCID 68494000HCID 68494000, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalyst2×HCID 1140TolueneSolvent

Procedure

Paraformaldehyde (6.32 g) was added portionwise to a solution of 211 (2.21 g, 7.04 mmol) in toluene (55 ml) with pTSA (60 mg). The reaction mixture was heated under reflux for 2 h. Further paraformaldehyde (632 mg) was added and heating under reflux was continued overnight. Additional pTSA (60 mg) and paraformaldehyde (1.9 g) was added to the reaction mixture portionwise over 2 h. The solution was cooled to rt, water (50 ml) and ethyl acetate (60 ml) were added. The layers were separated and the organic layer was washed with water (2×50 ml) and brine (50 ml), dried (MgSO4) and concentrated in vacuo to afford the title compound (2.15 g, 94%) as a colourless oil. 1H NMR indicated a mixture of conformers, signals for both conformers are listed 1.04, 1.12 (3H, d, J=6.7 Hz, CH3CH), 2.14, 2.17 (3H, s, CH3CO), 2.38-2.51 (1H, m, CHH for both conformers), 2.89-3.06 (1H, m, CHH for both conformers), 3.84, 3.85 (3H, s, OCH3), 4.06-4.6 (2H, m, CH2 for both conformers), 5.01-5.02 (3H, m, CHCH3 and CH2Ph for both conformers), 6.6-6.64 (2H, m, 2×CH for both conformers), 7.28-7.44 (5H, m, 5×CH, phenyl for both conformers). LC/MS (ES+) tr=1.02 min, m/z 348.19 (M++Na).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 2 h
  3. temperatureheating
  4. temperatureunder reflux
  5. customThe layers were separated
  6. washthe organic layer was washed with water (2×50 ml) and brine (50 ml)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8c5989e2c4cb4926a808d6c68420b3fd
Source dataset
uspto-grants-2013_03
Patent number
US08394825B2

Reaction notes

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