Chloroform → HCID 23062430, compound

HRID 2109379Notes

Reaction equation

HRID 2109379 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.[Si]([O:31][CH2:32][C:33]1[C:34]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[C:35]([C:38]([O:40][CH3:41])=[O:39])[O:36][CH:37]=1)(C(C)(C)C)(C)C.C(Cl)(Cl)Cl>O>[OH:31][CH2:32][C:33]1[C:34]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[C:35]([C:38]([O:40][CH3:41])=[O:39])[O:36][CH:37]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 23062518HCID 23062518, compound

Product 1

HCID 23062430HCID 23062430, compoundYield 67.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Tetrabutylammonium fluoride (1 M THF solution: 7.62 ml) was added at 25° C. to a THF (10 ml) solution of methyl 4-(tert-butyldimethylsilyloxymethyl)-3-phenyl-2-furancarboxylate (2.20 g), and stirred for 0.5 hours. Chloroform and water were added to the reaction solution, the organic layer was dried over MgSO4, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: 0%→30% ethyl acetate/hexane gradient, thereby giving 1.00 g of the desired compound.

Workup

  1. dry with materialthe organic layer was dried over MgSO4
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (eluent

Sources & evidence

ORD record
ord-c1e59bea54c44deda1ecbd798b2475d9
Source dataset
uspto-grants-2009_04
Patent number
US07514452B2

Reaction notes

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