Tetrabutylammonium Fluoride → HCID 13216467, compound

HRID 371447Notes

Reaction equation

HRID 371447 reaction equation
[CH3:1][O:2][C:3](=[O:32])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[O:12][C:11]2[CH2:13][C@@H:14]([O:25][CH:26]3[CH2:31][CH2:30][CH2:29][CH2:28][O:27]3)[C@H:15]([CH2:16][O:17][Si](C(C)(C)C)(C)C)[C:10]=2[CH:9]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:1][O:2][C:3](=[O:32])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[O:12][C:11]2[CH2:13][C@@H:14]([O:25][CH:26]3[CH2:31][CH2:30][CH2:29][CH2:28][O:27]3)[C@H:15]([CH2:16][OH:17])[C:10]=2[CH:9]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57311126HCID 57311126, compound

Product 1

HCID 13216467HCID 13216467, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 900 mg of the furan derivative produced in Example 12 in 120 ml of absolute tetrahydrofuran is combined with 960 mg of tetrabutylammonium fluoride dissolved in 10 ml of tetrahydrofuran, and the mixture is stirred under argon at room temperature for 1 hour. Thereafter the reaction solution is precipitated into ice water, and the aqueous phase is extracted repeatedly with ether. The organic phases are combined, washed with water and then with semisaturated sodium chloride solution, dried over magnesium sulfate, and concentrated. The crude product is chromatographed over 60 g of silica gel in a hexane/20% acetone-hexane gradient, thus obtaining 648 mg of the title compound as an oil.

Workup

  1. customThereafter the reaction solution is precipitated into ice water
  2. extractionthe aqueous phase is extracted repeatedly with ether
  3. washwashed with water
  4. dry with materialwith semisaturated sodium chloride solution, dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe crude product is chromatographed over 60 g of silica gel in a hexane/20% acetone-hexane gradient

Sources & evidence

ORD record
ord-589a5254e0034a2d9db29f79350e8ae9
Source dataset
uspto-grants-1985_07
Patent number
US04532236

Reaction notes

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