Methanol → HCID 70633216, compound

HRID 1729899Notes

Reaction equation

HRID 1729899 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 mixtrue 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°; λKBr 5.85μ; τCDCl 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-2ead1e9e15c94741a11eab3fff4b5e31
Source dataset
uspto-grants-1976_11
Patent number
US03989841

Reaction notes

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