Tetrabutylammonium Fluoride → HCID 69246297, compound

HRID 2371103Notes

Reaction equation

HRID 2371103 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.CC([Si](C)(C)[O:24][CH2:25][CH2:26][CH:27]([CH:35]([O:45][CH2:46][C:47]1[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[CH:49][CH:48]=1)[CH2:36][CH2:37][C:38]1[CH:43]=[CH:42][C:41]([Br:44])=[CH:40][CH:39]=1)[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])(C)C>O1CCCC1>[OH:24][CH2:25][CH2:26][CH:27]([CH:35]([O:45][CH2:46][C:47]1[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[CH:49][CH:48]=1)[CH2:36][CH2:37][C:38]1[CH:39]=[CH:40][C:41]([Br:44])=[CH:42][CH:43]=1)[C:28]([O:30][C:31]([CH3:32])([CH3:34])[CH3:33])=[O:29]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66671420HCID 66671420, compound

Product 1

HCID 69246297HCID 69246297, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tetra-n-butylammonium fluoride (0.45 ml) was added dropwise over 15 minutes to a stirred solution of the compound (200 mg) obtained from step 4 above in tetrahydrofuran (5 ml) at 0° C. under nitrogen atmosphere. The reaction mixture was allowed to warm to room temperature at which stirring was continued for 2 hour. The volatiles were evaporated under reduced pressure and the residue thus obtained was partitioned between ethyl acetate and water. The phases were separated and the aqueous layer was washed with ethyl acetate. The organic layers were combined, washed with water and brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure to furnish the title compound (120 mg).

Workup

  1. customThe volatiles were evaporated under reduced pressure
  2. customthe residue thus obtained
  3. customwas partitioned between ethyl acetate and water
  4. customThe phases were separated
  5. washthe aqueous layer was washed with ethyl acetate
  6. washwashed with water and brine
  7. dry with materialdried over anhydrous sodium sulphate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-aa2ebbf1096a4dbbb1095821a91a9815
Source dataset
uspto-grants-2014_04
Patent number
US08710261B2

Reaction notes

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