Tetrahydrofuran → HCID 131720776, compound

HRID 1957696Notes

Reaction equation

HRID 1957696 reaction equation
C[Si](C)(C)C#C[CH:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19])=[C:9]([C:20]23[CH2:29][CH:24]4[CH2:25][CH:26]([CH2:28][CH:22]([CH2:23]4)[CH2:21]2)[CH2:27]3)[CH:8]=1)[OH:6].[CH2:32]1COC[CH2:33]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O>[C:32]([CH:16]([O:15][CH2:14][O:13][C:10]1[CH:11]=[CH:12][C:7]([CH2:5][OH:6])=[CH:8][C:9]=1[C:20]12[CH2:21][CH:22]3[CH2:28][CH:26]([CH2:25][CH:24]([CH2:23]3)[CH2:29]1)[CH2:27]2)[CH2:17][O:18][CH3:19])#[CH:33]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 131720777HCID 131720777, compound

Product 1

HCID 131720776HCID 131720776, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4.7 g (10.5 mmol) of a-trimethylsilylethynyl-3-(1-adamantyl)-4-methoxyethoxymethoxyphenylmethanol and 50 ml of THF were introduced into a round-bottomed flask and 11.4 ml (12.6 mmol) of tetrabutylammonium fluoride solution (1.1M in THF) was added dropwise. The reaction medium was stirred at room temperature for one hour and was then poured into water and extracted with ethyl ether. The organic phase was separated out after settling had taken place, dried over magnesium sulfate and evaporated. The residue obtained was purified by chromatography on a column of silica, eluted with a mixture of ethyl acetate and heptane (30/70). After evaporation of the solvents, 2.5 g (64%) of a-ethynyl-3-(1-adamantyl)-4-methoxyethoxymethoxyphenyl-methanol were recovered.

Workup

  1. extractionextracted with ethyl ether
  2. customThe organic phase was separated out
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue obtained
  6. customwas purified by chromatography on a column of silica
  7. washeluted with a mixture of ethyl acetate and heptane (30/70)
  8. customAfter evaporation of the solvents, 2.5 g (64%) of a-ethynyl-3-(1-adamantyl)-4-methoxyethoxymethoxyphenyl-methanol
  9. customwere recovered

Sources & evidence

ORD record
ord-15efebcda3db4339a1bd0360d1537a5a
Source dataset
uspto-grants-1998_07
Patent number
US05786379

Reaction notes

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