Formaldehyde → HCID 54100857, compound

HRID 365885Notes

Reaction equation

HRID 365885 reaction equation
[C:1]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][O:14][C:15]1[CH:16]=[N:17][C:18]([Cl:23])=[C:19]([CH:21]=[CH2:22])[CH:20]=1)(OC(C)(C)C)=O.C=O.[OH-].[Na+]>C(O)=O>[Cl:23][C:18]1[N:17]=[CH:16][C:15]([O:14][CH2:13][C@H:9]2[CH2:10][CH2:11][CH2:12][N:8]2[CH3:1])=[CH:20][C:19]=1[CH:21]=[CH2:22]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 22961814HCID 22961814, compound

Product 1

HCID 54100857HCID 54100857, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
70 °C

Procedure

To the product from 167a (328 mg, 0.97 mmol) was added formic acid (88%, 3 mL) and formaldehyde (37%, 6 mL). The mixture was stirred and heated at 70° C. for 6 h. After cooling to room temperature, the mixture was basified with aqueous 10% NaOH. The solution was then extracted with CH2Cl2 (3X), the combined organic layers were dried (MgSO4), concentrated and chromatographed (silica gel; CH2Cl2, 10:0.3 to 10:1) to afford an oil (130 mg, 53%): 1H NMR (CDCl3, 300 MHz) δ 1.70-1.90 (m, 3H), 2.02 (m, 1H), 2.32 (m, 1H), 2.48 (s, 3H), 2.66 (m, 1H), 3.12 (m, 1H), 3.98 (m, 2H), 5.48 (d, 1H, J=10.5 Hz), 5.76 (d, 1H, J=17.5 Hz), 6.98 (dd, 1H, J=11.0, 17.5 Hz), 7.40 (d, 1H, J=3.0 Hz), 8.00 (d, 1H, J=3.0 Hz); MS (CI/NH3) m/z 253 (M+H)+.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionThe solution was then extracted with CH2Cl2 (3X)
  3. dry with materialthe combined organic layers were dried (MgSO4)
  4. concentrationconcentrated
  5. customchromatographed (silica gel; CH2Cl2, 10:0.3 to 10:1)

Sources & evidence

ORD record
ord-2a1f0dcccce145b98797e4c4466b689d
Source dataset
uspto-grants-2000_10
Patent number
US06127386

Reaction notes

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