Methanol → HCID 70633216, compound

HRID 972262Notes

Reaction equation

HRID 972262 reaction equation
[OH:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH:7]=[CH:8][C:9]([CH2:15][C:16]([OH:18])=[O:17])=[CH:10][C:11]=3[CH2:12]2)=[CH:4][CH:3]=1.CO.[N+](=[CH2:23])=[N-]>CCOCC.C(O)(=O)C>[CH3:23][C:10]1[C:11]2[CH2:12][C:13]3[C:5](=[CH:4][CH:3]=[C:2]([OH:1])[CH:14]=3)[C:6]=2[CH:7]=[CH:8][C:9]=1[CH2:15][C:16]([OH:18])=[O:17]

Participants

6

Reactant 3

HCID 887MethanolHCID 9550DiazomethaneHCID 21406505HCID 21406505, compound

Product 1

HCID 70633216HCID 70633216, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 83mg. of 7-hydroxyfluorene-2-acetic acid in 2ml. of methanol and 5ml. of ether is treated with an excess of diazomethane in ether. After 20 min. at room temperature, the mixture is treated with several drops of acetic acid and evaporated. The residue is plate chromatographed on silica gel using chloroform as the developing solvent. The major band (UV) is eluted with ethyl acetate, evaporated, and the residue crystallized from acetone-isopropyl ether to give 36mg. of the title compound, mp 135.5°-136.5°. The analytical sample is prepared by recrystallization from acetone-isopropyl ether, mp 136-137°; λ KBr 5.85μ; τCDCl3 TMS 6.31 (S, 2-CH2CO2CH3).

Workup

  1. customevaporated
  2. customchromatographed on silica gel
  3. washThe major band (UV) is eluted with ethyl acetate
  4. customevaporated
  5. customthe residue crystallized from acetone-isopropyl ether
  6. customto give 36mg

Sources & evidence

ORD record
ord-16eed5f583ee454f92150b08017e341d
Source dataset
uspto-grants-1977_10
Patent number
US04052436

Reaction notes

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