Tetrabutylammonium Fluoride → HCID 15840681, compound

HRID 342755Notes

Reaction equation

HRID 342755 reaction equation
[Si]([O:8][C:9]1[C:18]([CH2:19][CH2:20][CH3:21])=[C:17]2[C:12]([C:13]([CH2:23][CH3:24])=[CH:14][C:15](=[O:22])[O:16]2)=[CH:11][CH:10]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH2:23]([C:13]1[C:12]2[C:17](=[C:18]([CH2:19][CH2:20][CH3:21])[C:9]([OH:8])=[CH:10][CH:11]=2)[O:16][C:15](=[O:22])[CH:14]=1)[CH3:24]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 15840680HCID 15840680, compound

Product 1

HCID 15840681HCID 15840681, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-tert-butyldimethylsilyloxy-4-ethyl-8-propylcoumarin (Step B; 117 mg, 0.3382 mmol) in five mL of tetrahydrofuran (THF) was added a 1.0M solution of tetrabutylammonium fluoride (0.51 mL, 0.51 mmol). The mixture was stirred at ambient temperature for five minutes and subsequently quenched by the addition of saturated ammonium chloride. The mixture was extracted several times with ethyl acetate and the combined organic extracts were dried over magnesium sulfate, filtered, concentrated in vacuo, and the crude residue was purified by flash chromatography on silica gel (gradient elution: 10% then 20% then 30% ethyl acetate/hexane) which yielded the title compound.

Workup

  1. customsubsequently quenched by the addition of saturated ammonium chloride
  2. extractionThe mixture was extracted several times with ethyl acetate
  3. dry with materialthe combined organic extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customthe crude residue was purified by flash chromatography on silica gel (
  7. washgradient elution

Sources & evidence

ORD record
ord-a5b36cc91f504fdc8275e8cd3a3db8a7
Source dataset
uspto-grants-1999_01
Patent number
US05859051

Reaction notes

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