Tetrabutylammonium Fluoride → HCID 54025217, compound

HRID 342009Notes

Reaction equation

HRID 342009 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([C@@H:20]([S:41][CH2:42][CH2:43][CH2:44][C:45]([OH:48])([CH3:47])[CH3:46])[CH2:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[C@@H:29]([CH2:39][CH3:40])[C:30]([O:32]CC[Si](C)(C)C)=[O:31])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([C@@H:20]([S:41][CH2:42][CH2:43][CH2:44][C:45]([OH:48])([CH3:47])[CH3:46])[CH2:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[C@@H:29]([CH2:39][CH3:40])[C:30]([OH:32])=[O:31])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 53645409HCID 53645409, compound

Product 1

HCID 54025217HCID 54025217, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of the ester of Step 8 (4.25 g, 60 mmol) in THF (43 mL) at r.t. was added the 1M nBu4NF solution (18 mL, 180 mmol). The solution was stirred at 50° C. for 1 h, and was then concentrated under vacuum to give a brown residue which was purified directly by flash chromatography. Elution was effected with 1:10 EtOAc:toluene containing 1% HOAc, followed by 1:5 EtOAc:toluene containing 1% HOAc to give the title compound as a yellow foam (3.6 g).

Workup

  1. concentrationwas then concentrated under vacuum
  2. customto give a brown residue which
  3. customwas purified directly by flash chromatography
  4. washElution

Sources & evidence

ORD record
ord-eab560e026ae4b98afc95a2f022d0eea
Source dataset
uspto-grants-1999_01
Patent number
US05856322

Reaction notes

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