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Citric Acid → HCID 21967941, compound

HRID 1003941
Notes
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Reaction equation

HRID 1003941 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([CH2:10][CH2:11][C:12]([C:14]3[C:19]([O:20][CH2:21][CH:22]=[CH2:23])=[CH:18][C:17]([CH3:24])=[CH:16][C:15]=3[O:25][C@@H:26]3[O:34][C@H:33]([CH2:35][OH:36])[C@@H:31]([OH:32])[C@H:29]([OH:30])[C@H:27]3[OH:28])=[O:13])[CH:8]=[CH:9][C:2]1=2.N1C(C)=CC(C)=CC=1C.[P:46](Cl)([O:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)([O:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)=[O:47].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[O:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([CH2:10][CH2:11][C:12]([C:14]3[C:19]([O:20][CH2:21][CH:22]=[CH2:23])=[CH:18][C:17]([CH3:24])=[CH:16][C:15]=3[O:25][C@@H:26]3[O:34][C@H:33]([CH2:35][O:36][P:46]([O:48][C:49]4[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=4)([O:55][C:56]4[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=4)=[O:47])[C@@H:31]([OH:32])[C@H:29]([OH:30])[C@H:27]3[OH:28])=[O:13])[CH:8]=[CH:9][C:2]1=2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 311Citric AcidHCID 79532,4,6-TrimethylpyridineHCID 75654Diphenyl chlorophosphateHCID 10601391HCID 10601391, compound

Product 1

HCID 21967941HCID 21967941, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

3-(5-Benzo[b]furanyl)-2'-(β-D-glucopyranosyloxy)-6'-allyloxy-4'-methylpropiophenone (300 mg) obtained in Example 2 is dissolved in tetrahydrofuran (3 ml), and thereto are added 2,4,6-collidine (315 mg) and diphenyl chlorophosphate (486 mg) under ice-cooling. The mixture is stirred at room temperature for 22 hours under argon atmosphere. The reaction mixture is poured into chilled 10% aqueous citric acid solution, and extracted with ethyl acetate. The organic layer is washed successively with water, a saturated aqueous sodium hydrogen carbonate solution, and a saturated aqueous sodium chloride solution, dried, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (solvent; chloroform/methanol) to give 3-(5-benzo[b]furanyl)-2'-(6-O-diphenylphosphono-β-D-glucopyranosyloxy)-6'-allyloxy-4'-methylpropiophenone (327 mg).

Workup

  1. temperaturecooling
  2. additionThe reaction mixture is poured
  3. extractionextracted with ethyl acetate
  4. washThe organic layer is washed successively with water
  5. dry with materiala saturated aqueous sodium hydrogen carbonate solution, and a saturated aqueous sodium chloride solution, dried
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by silica gel column chromatography (solvent; chloroform/methanol)

Sources & evidence

ORD record
ord-463a7b61bf344a2b95d9db2ea7ae663c
Source dataset
uspto-grants-2000_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06048842

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes