Diazomethane → HCID 86602834, compound

HRID 1743946Notes

Reaction equation

HRID 1743946 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:12][C:11](=[CH2:13])[CH2:10][C@H:9]2[C:14]([OH:16])=[O:15])=[CH:4][CH:3]=1.[N+](=[CH2:19])=[N-]>CO.C(OCC)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]2[CH2:12][C:11](=[CH2:13])[CH2:10][C@H:9]2[C:14]([O:16][CH3:19])=[O:15])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 68516847HCID 68516847, compound

Product 1

HCID 86602834HCID 86602834, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A 100 mL round bottom flask was equipped with a magnetic stir bar and charged with a solution of 1.188 g (5.02 mmol) of the product from Step A (the combined product of two experiments) dissolved in 20 mL of methanol was stirred and cooled to 0° C. with an external ice-water bath. A solution of diazomethane in diethyl ether was added slowly until the reaction mixture developed the persistent yellow color and TLC analysis (25% ethyl acetate-hexanes) indicated that esterification was complete. Excess diazomethane was quenched by dropwise addition of acetic acid, and volatiles were removed in vacuo. The residual clear oil was used directly in the next step without further purification.

Workup

  1. customA 100 mL round bottom flask was equipped with a magnetic stir bar
  2. customExcess diazomethane was quenched by dropwise addition of acetic acid, and volatiles
  3. customwere removed in vacuo
  4. customThe residual clear oil was used directly in the next step without further purification

Sources & evidence

ORD record
ord-757609d24120409f8fa7e9e4a6c7746b
Source dataset
uspto-grants-2006_03
Patent number
US07012084B2

Reaction notes

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