Diazomethane → HCID 15052381, compound

HRID 2107021Notes

Reaction equation

HRID 2107021 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[C:5]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][OH:20])[CH:6]=[C:7]([S:10][CH3:11])[C:8]=1[OH:9].[N+](=[CH2:23])=[N-]>C(Cl)(Cl)Cl.CCOCC.C(O)(=O)C>[CH3:11][S:10][C:7]1[CH:6]=[C:5]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][OH:20])[CH:4]=[C:3]([S:2][CH3:1])[C:8]=1[O:9][CH3:23]

Participants

6

Reactant 2

HCID 9550DiazomethaneHCID 14600609HCID 14600609, compound

Product 1

HCID 15052381HCID 15052381, compoundYield 62%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

320 mg of compound 1 was dissolved in chloroform and 10 ml of a solution of diazomethane in ether (about 0.5M) was added thereto dropwise at 0° C. After stirring at 0° C. for 6 hours, several drops of acetic acid were added thereto. After the completion of the reaction, the mixture was extracted with ether. The extract was concentrated and subjected to column chyromatography (silica gel, ethyl acetate: hexane=1:5-1:4). As a result, 206 mg of the desired compound was obtained (yield: 62%).

Workup

  1. customdropwise at 0° C
  2. customAfter the completion of the reaction
  3. extractionthe mixture was extracted with ether
  4. concentrationThe extract was concentrated

Sources & evidence

ORD record
ord-f80675b6417f42c49149b4ebcbe68e86
Source dataset
uspto-grants-1990_06
Patent number
US04933329

Reaction notes

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