Tetrabutylammonium Fluoride → HCID 19966471, compound

HRID 1756340Notes

Reaction equation

HRID 1756340 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:19]([O:22][CH:23]([C:29]1[CH:34]=[CH:33][CH:32]=[C:31](/[CH:35]=[CH:36]/[CH:37]=[CH:38]/[CH:39]([O:48][C:49](=[O:51])[CH3:50])[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[CH:30]=1)[CH2:24][CH2:25][CH2:26][CH2:27][OH:28])(=[O:21])[CH3:20].[Si](O[Si](C(C)(C)C)(C)C)(C(C)(C)C)(C)C>O1CCCC1.CCOCC>[C:19]([O:22][CH:23]([C:29]1[CH:34]=[CH:33][CH:32]=[C:31](/[CH:35]=[CH:36]/[CH:37]=[CH:38]/[CH:39]([O:48][C:49](=[O:51])[CH3:50])[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[CH:30]=1)[CH2:24][CH2:25][CH2:26][CH2:27][OH:28])(=[O:21])[CH3:20]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86748884HCID 86748884, compound

Product 1

HCID 19966471HCID 19966471, compoundYield 59.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
24 °C

Procedure

914 mg of tetrabutylammonium fluoride is added to a solution of 500 mg of (5RS)-5-acetoxy-5-{3-[(1E,3E)-(5RS)-5-acetoxy-1,3-tridecadienyl]-phenyl}-pentan-1-ol-tert-butyldimethylsilylether in 28 ml of tetrahydrofuran at 0° C., stirred for 30 minutes at 0° C. and for 4.5 hours at 24° C. Then, it is diluted with ether, washed with brine, dried on sodium sulfate and concentrated by evaporation in a vacuum. The residue is chromatographed on silica gel. With hexane/0-20% ethyl acetate, 193 mg of (5RS)-5-acetoxy-5-{3-{(1E,3E)-(5RS)-5-acetoxy-1,3-tridecadienyl}-phenyl}-pentan-1-ol is obtained as colorless oil.

Workup

  1. washwashed with brine
  2. customdried on sodium sulfate
  3. concentrationconcentrated by evaporation in a vacuum
  4. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-47c5067a23bd4c739078bf144ff38c9f
Source dataset
uspto-grants-1995_08
Patent number
US05440044

Reaction notes

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