Methanol → HCID 10271985, compound

HRID 2120467Notes

Reaction equation

HRID 2120467 reaction equation
[Si]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH2:25][CH2:26][C:27]2[CH:28]=[C:29](/[C:33](/[CH3:43])=[CH:34]/[CH:35]=[CH:36]/[C:37]([CH2:41][CH3:42])([OH:40])[CH2:38][CH3:39])[CH:30]=[CH:31][CH:32]=2)[CH:13]=[CH:14][C:15]=1[CH2:16][O:17][Si](C(C)(C)C)(C)C)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.CO>C1COCC1>[OH:8][CH2:9][C:10]1[CH:11]=[C:12]([CH2:25][CH2:26][C:27]2[CH:28]=[C:29](/[C:33](/[CH3:43])=[CH:34]/[CH:35]=[CH:36]/[C:37]([CH2:38][CH3:39])([OH:40])[CH2:41][CH3:42])[CH:30]=[CH:31][CH:32]=2)[CH:13]=[CH:14][C:15]=1[CH2:16][OH:17]

Participants

5

Reactant 3

HCID 887MethanolHCID 2724141Tetrabutylammonium FluorideHCID 23439894HCID 23439894, compound

Product 1

HCID 10271985HCID 10271985, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

340 mg of (4E,6E)-7-(3-{2-[3,4-bis-(tert-butyldimethylsilanyloxymethyl)phenyl]ethyl}phenyl)-3-ethylocta-4,6-dien-3-ol (0.5 mmol) are dissolved in 10 ml of THF and 1.5 ml (1.5 mmol) of a tetrabutylammonium fluoride solution (1M in THF) are added dropwise. After 30 minutes, 10 ml of methanol are added and the mixture is concentrated under reduced pressure. After purification of the residue by chromatography on a silica column, a colourless oil is obtained (m=163 mg; Y=88%).

Workup

  1. concentrationthe mixture is concentrated under reduced pressure
  2. customAfter purification of the residue by chromatography on a silica column
  3. customa colourless oil is obtained (m=163 mg; Y=88%)

Sources & evidence

ORD record
ord-8ff4c476d2d34c88beafbc47bc0487f6
Source dataset
uspto-grants-2004_02
Patent number
US06689922B1

Reaction notes

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