Water → HCID 86630343, compound

HRID 217626Notes

Reaction equation

HRID 217626 reaction equation
[Si]([O:8][C@@H:9]1[C@H:17]2[C@@:13]([CH3:29])([C@@H:14]([C@@:18]3([CH3:28])[O:22][CH2:21][C@@H:20]([CH2:23][C:24]([CH3:27])([OH:26])[CH3:25])[CH2:19]3)[CH2:15][CH2:16]2)[CH2:12][CH2:11][CH2:10]1)(C(C)(C)C)(C)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-].O.CCOC(C)=O>C1COCC1>[OH:26][C:24]([CH3:27])([CH3:25])[CH2:23][C@@H:20]1[CH2:21][O:22][C@@:18]([C@@H:14]2[C@:13]3([CH3:29])[C@H:17]([C@@H:9]([OH:8])[CH2:10][CH2:11][CH2:12]3)[CH2:16][CH2:15]2)([CH3:28])[CH2:19]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 57696851HCID 57696851, compound

Product 1

HCID 86630343HCID 86630343, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 13 (330 mg, 0.78 mmol) in dry THF (4 mL) was treated with nBu4NF (1.02 g, 3.25 mmol). The mixture was heated at reflux for 90 h. H2O (20 mL) and EtOAc (20 mL) were added. The aqueous layer was extracted with EtOAc (4×20 mL) and the combined organic layer was dried (Na2SO4) and concentrated in vacuum. The residue was purified by flash chromatography (SiO2, 2×5.5 cm, 30% EtOAc-hexanes) to give 13a (224 mg, 93%, white solid, mp: 98° C.).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 90 h
  3. extractionThe aqueous layer was extracted with EtOAc (4×20 mL)
  4. dry with materialthe combined organic layer was dried (Na2SO4)
  5. concentrationconcentrated in vacuum
  6. customThe residue was purified by flash chromatography (SiO2, 2×5.5 cm, 30% EtOAc-hexanes)

Sources & evidence

ORD record
ord-4fb1f5e66ffd4b1bb886951401ad077b
Source dataset
uspto-grants-2012_06
Patent number
US08198263B2

Reaction notes

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