Diazomethane → HCID 13488554, compound

HRID 463550Notes

Reaction equation

HRID 463550 reaction equation
[N+](=[CH2:3])=[N-].[F:4][C:5]([F:31])([F:30])[C:6]1[CH:29]=[CH:28][C:9]([O:10][C:11]2[CH:27]=[CH:26][C:14]([O:15][CH:16]([CH3:25])[CH:17]([OH:24])[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:13][CH:12]=2)=[CH:8][CH:7]=1>CCOCC>[F:4][C:5]([F:30])([F:31])[C:6]1[CH:7]=[CH:8][C:9]([O:10][C:11]2[CH:27]=[CH:26][C:14]([O:15][CH:16]([CH3:25])[CH:17]([O:24][CH3:3])[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:13][CH:12]=2)=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 12856783Ethyl 4-[4-(4-trifluoromethylphenoxy)phenoxy]-3-hydroxypentanoate

Product 1

HCID 13488554HCID 13488554, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Diazomethane (2.8 g) in ether (100 ml) is added to ethyl 4-[4-(4-trifluoromethylphenoxy)phenoxy]-3-hydroxypentanoate (1.88 g, 3.75 mmol) in ether (5 ml) under N2 and in an ice bath. Small amounts of chromatographic silica gel are added to the mixture in the ice bath until the color disappears. The mixture is then stirred overnight with cooling. The silica gel is removed by filtration and the organic phase is dried and concentrated. The crude product is purified by preparative thin layer chromatography to yield ethyl 4-[4-(4-trifluoromethylphenoxy)phenoxy]-3-methoxypentanoate (cpd. 1 in Table A). MS m/e 412 (m+).

Workup

  1. temperaturewith cooling
  2. customThe silica gel is removed by filtration
  3. customthe organic phase is dried
  4. concentrationconcentrated
  5. customThe crude product is purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-a5ecd829d2c64042b14c2927f14178f8
Source dataset
uspto-grants-1985_05
Patent number
US04520199

Reaction notes

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