Diazomethane → HCID 71038074, compound

HRID 2361709Notes

Reaction equation

HRID 2361709 reaction equation
[N+](=[CH2:3])=[N-].[O:4]=[C:5]1[CH:12]2[CH2:13][C:8]3([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:9][CH:10]([CH2:14][CH:6]1[CH2:7]3)[CH2:11]2.[OH-].[K+]>CO.O>[O:4]=[C:5]1[CH2:3][CH:6]2[CH2:7][C:8]3([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:20])([CH3:19])[CH3:21])[CH2:9][CH:10]([CH2:11][CH:12]1[CH2:13]3)[CH2:14]2

Participants

6

Reactant 3

HCID 9550DiazomethaneHCID 14797Potassium HydroxideHCID 58192767HCID 58192767, compound

Product 1

HCID 71038074HCID 71038074, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of diazomethane (Diazald, 3.97 mmol) was added dropwise to a cold (0° C.) solution of ketone 1C (0.886 mmol) and KOH (40 mmol) in MeOH (10 mL) and water (2 mL) over a period of 3 h. The reaction mixture was allowed to warm to rt and was maintained for 16 h. The resulting white-grey suspension was concentrated and the residue was partitioned between water (10 mL) and DCM (10 mL). The layers were separated and the aqueous layer was extracted with DCM (2×10 mL). The combined organic extracts were dried (Na2SO4) and the solvent was evaporated to yield ketone 1D in 90% yield. The ketone was used in the next step without further purification. Data: LC/MS (ESR) m/z 280 [M+1]+.

Workup

  1. temperaturewas maintained for 16 h
  2. concentrationThe resulting white-grey suspension was concentrated
  3. customthe residue was partitioned between water (10 mL) and DCM (10 mL)
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with DCM (2×10 mL)
  6. dry with materialThe combined organic extracts were dried (Na2SO4)
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-020c729bf91147a1a428f084d28ae03a
Source dataset
uspto-grants-2014_04
Patent number
US08691808B2

Reaction notes

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