Formaldehyde → HCID 53312154, compound

HRID 924346Notes

Reaction equation

HRID 924346 reaction equation
[H-].[Na+].[C:3]([C@@H:11]1[CH2:15][CH:14]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:19][CH:18]=2)[N:13](/[CH:29]=[CH:30]/[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:12]1=[O:37])(=O)C1C=CC=CC=1.C=O>C1(C)C=CC=CC=1>[C:20]1([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:19]=[CH:18][C:17]([CH2:16][C@H:14]2[N:13](/[CH:29]=[CH:30]/[C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:12](=[O:37])[C:11](=[CH2:3])[CH2:15]2)=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 24758Sodium hydrideHCID 86673650HCID 86673650, compound

Product 1

HCID 53312154HCID 53312154, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of sodium hydride (2.03 g, 46.3 mmol) in 40 mL of anhydrous toluene is cooled to 0° C. by ice bath, add a solution of (S)-3-Benzoyl-5-biphenyl-4-ylmethyl-1-((E)-but-1-enyl)-pyrrolidin-2-one (4a, R1=1-butenyl, R4=phenyl) (14.7 g, 35.7 mmol) in anhydrous toluene dropwise, stir for 30 min, then add paraformaldehyde (2.2 g, 71.4 mmol) in portions, heat to reflux under nitrogen atmosphere for 4 h, cool to room temperature, quench with saturated NH4Cl aqueous solution, extract with toluene, the combined organic extracts are washed with saturated Na2CO3 aqueous solution and brine, dry over anhydrous Na2SO4 and concentrate to obtain (R)-5-Biphenyl-4-ylmethyl-1-((E)-but-1-enyl)-3-methylene-pyrrolidin-2-one (1a, R1=1-butenyl). 1HNMR (400 MHz, CDCl3): 1.07 (t, 3H, CH3H), 2.12 (m, 2H, CH2H), 2.57 (m, 2H, 3-CH2), 2.65 (m, 1H, 5-CH2), 3.16 (m, 1H, 5-CH2), 4.14 (m, 1H, 4-CH), 5.22 (s, 1H, C═CHH), 5.27 (m, 1H, CH═CH), 5.91 (d, 1H, HC═CHH), 6.85 (d, 1H, HC═CH—N), 7.14˜7.51 (9H, m, aromatic).

Workup

  1. temperatureto reflux under nitrogen atmosphere for 4 h
  2. temperaturecool to room temperature
  3. customquench with saturated NH4Cl aqueous solution
  4. extractionextract with toluene
  5. washthe combined organic extracts are washed with saturated Na2CO3 aqueous solution and brine
  6. dry with materialdry over anhydrous Na2SO4
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-85cfa58b20ba45f9b6dd96ae87d33c45
Source dataset
uspto-grants-2016_03
Patent number
US09278908B2

Reaction notes

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