Tetrahydrofuran → HCID 89768220, compound

HRID 591575Notes

Reaction equation

HRID 591575 reaction equation
[Cl:1][C:2]1[CH:23]=[C:22]([O:24][Si](C(C)C)(C(C)C)C(C)C)[CH:21]=[CH:20][C:3]=1[CH2:4][O:5][C:6]1[CH:19]=[CH:18][C:9]2[CH:10]([CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH2:11][O:12][C:8]=2[CH:7]=1.C1COCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl-].[Na+].O.CCOC(C)=O>[Cl:1][C:2]1[CH:23]=[C:22]([OH:24])[CH:21]=[CH:20][C:3]=1[CH2:4][O:5][C:6]1[CH:19]=[CH:18][C:9]2[CH:10]([CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH2:11][O:12][C:8]=2[CH:7]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 131734537HCID 131734537, compound

Product 1

HCID 89768220HCID 89768220, compoundYield 68.1%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a mixture of methyl 2-(6-((2-chloro-4-((triisopropylsilyl)oxy)benzyl)oxy)-2,3-dihydro-1-benzofuran-3-yl)acetate (5.70 g) and THF (50 mL) cooled with an ice bath was added tetrabutylammonium fluoride (1.0 M THF solution, 14.1 mL). After being stirred for 20 min, the mixture was diluted with brine and EtOAc. The layers were separated, and the aqueous layer was extracted with EtOAc. The combined organic layer was washed with brine, dried over MgSO4 and concentrated. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (2.68 g).

Workup

  1. temperaturecooled with an ice bath
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-dac8bb1e19f54357abe37f6fb9400230
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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