Water → HCID 86630344, compound

HRID 217628Notes

Reaction equation

HRID 217628 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 57696854HCID 57696854, compound

Product 1

HCID 86630344HCID 86630344, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 14 (280 mg, 0.78 mmol) in dry THF (4 mL) was treated with nBu4NF (1.05 g, 3.3 mmol). The mixture was heated at reflux. After 115 h H2O (20 mL) and EtOAc (20 mL) was added. The aqueous layer was extracted with EtOAc (4×20 mL) and the combined organic layer was dried (Na2SO4), filtered and concentrated in vacuum. The residue was purified by flash chromatography (SiO2, 2×5.5 cm, 30% EtOAc-hexanes) to give the corresponding diol 14a (180 mg, 88%, white solid, mp: 67° C.).

Workup

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

Sources & evidence

ORD record
ord-6b5085a664474d30a25c03d256a6695a
Source dataset
uspto-grants-2012_06
Patent number
US08198263B2

Reaction notes

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