Water → (3Z)-(5S)-5,9-Dimethyl-dec-3-ene-1,9-diol

HRID 493067Notes

Reaction equation

HRID 493067 reaction equation
C([Si](C)(C)[O:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[C@@H:11]([CH3:26])[CH2:12][CH2:13][CH2:14][C:15]([CH3:25])([O:17][Si](CC)(CC)CC)[CH3:16])(C)(C)C.F.O>C(Cl)Cl>[CH3:26][C@@H:11]([CH2:12][CH2:13][CH2:14][C:15]([CH3:25])([OH:17])[CH3:16])/[CH:10]=[CH:9]\[CH2:8][CH2:7][OH:6]

Participants

5

Reactant 3

HCID 962WaterHCID 14917Hydrofluoric AcidHCID 57680486(Z)-(S)-1-(t-Butyl-dimethyl-silanyloxy)-5,9-dimethyl-9-triethylsilanyloxy-dec-3-ene

Product 1

HCID 57680494(3Z)-(5S)-5,9-Dimethyl-dec-3-ene-1,9-diolYield 95.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of compound 12 (201 mg, 0.4 mmol) in anhydrous CH2Cl2 (10 mL) was added hydrofluoric acid (48%, 6 mL). After 40 minutes of stirring at room temperature, water was added, and the organic layer was separated, washed with water and NaHCO3, dried over MgSO4, and evaporated. The residue was chromatographed on silica Sep-Pak cartridge using hexane/EtOAc (6:4) as an eluent to give an oily diol 13 (76.4 mg, 92%).

Workup

  1. customthe organic layer was separated
  2. washwashed with water and NaHCO3
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customThe residue was chromatographed on silica Sep-Pak cartridge

Sources & evidence

ORD record
ord-7f4287cc60bc46afa4e8955e4e93c629
Source dataset
uspto-grants-2009_05
Patent number
US07534777B2

Reaction notes

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