Chloroform → HCID 13650575, compound

HRID 543412Notes

Reaction equation

HRID 543412 reaction equation
[CH2:1]([C:4]1[C:17]2[O:16][C:15]3[C:10](=[C:11]([F:18])[CH:12]=[CH:13][CH:14]=3)[C:9](=[O:19])[C:8]=2[CH:7]=[CH:6][C:5]=1[OH:20])[CH:2]=[CH2:3].ClC1C=CC=C(C(OO)=[O:29])C=1.C(Cl)(Cl)Cl.C(=O)([O-])[O-].[K+].[K+]>O>[F:18][C:11]1[C:10]2[C:9](=[O:19])[C:8]3[CH:7]=[CH:6][C:5]4[O:20][CH:2]([CH2:3][OH:29])[CH2:1][C:4]=4[C:17]=3[O:16][C:15]=2[CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 11430Potassium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 15617020HCID 15617020, compound

Product 1

HCID 13650575HCID 13650575, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-allyl-8-fluoro-3-hydroxy-9-oxo-9H-xanthene (1.4 g), m-chloroperbenzoic acid (1.2 g) and chloroform (250 ml) was stirred at room temperature for 5 hours and thereafter left to stand overnight. After addition of potassium carbonate (2 g) and water (50 ml), the mixture was extracted with chloroform. The chloroform layer was dried and the solvent was distilled off. The residue was recrystallized from ethanol to obtain 1.2 g of 7-fluoro-1,2-dihydro-2-hydroxymethyl-6-oxo-6H-furo[2,3-c]xanthene. m.p. 220°-221° C. This compound gave a mass spectrum having a molecular ion peak at m/e 286.

Workup

  1. waitleft
  2. waitto stand overnight
  3. extractionthe mixture was extracted with chloroform
  4. dry with materialThe chloroform layer was dried
  5. distillationthe solvent was distilled off
  6. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-47dde279ede54d968f3efa9a26d1e233
Source dataset
uspto-grants-1987_04
Patent number
US04661607

Reaction notes

Loading…