Tetrabutylammonium Fluoride → Ethyl 5-(3-acetyloxyphenylthio)-4-oxopentanoate

HRID 985479Notes

Reaction equation

HRID 985479 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:19]([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([S:29][Si](C(C)C)(C(C)C)C(C)C)[CH:24]=1)(=[O:21])[CH3:20].Br[CH2:41][C:42](=[O:50])[CH2:43][CH2:44][C:45]([O:47][CH2:48][CH3:49])=[O:46]>C1COCC1>[C:19]([O:22][C:23]1[CH:24]=[C:25]([S:29][CH2:41][C:42](=[O:50])[CH2:43][CH2:44][C:45]([O:47][CH2:48][CH3:49])=[O:46])[CH:26]=[CH:27][CH:28]=1)(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 112210453-[1,1-bis (Methylethyl)-2-methyl-1-silapropylthio]phenyl acetateHCID 12397184Ethyl 5-bromo-4-oxopentanoate

Product 1

HCID 11426889Ethyl 5-(3-acetyloxyphenylthio)-4-oxopentanoateYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Tetrabutylammonium fluoride (7 ml, 7.0 mmol, 1M in THF) was added to a solution of 3-[1,1-bis(Methylethyl)-2-methyl-1-silapropylthio]phenyl acetate (1.53 g, 4.7 mmol) in THF (10 ml) under argon at room temperature. The reaction was stirred for 15 minutes followed by addition of a solution of ethyl 5-bromo-4-oxopentanoate (1.15 g, 5.17 mmol) in THF (5 ml). After stirring for 3 hours, the solvent was removed under vacuum and the crude product was chromatographed over silica gel to yield 920 mg (73%) of ethyl 5-(3-acetyloxyphenylthio)-4-oxopentanoate. NMR 1H Cl3CD δ: 7.29 (t, 1H, J=8.0 Hz), 7.18 (dd, 1H, J=0.8, 7.6 Hz), 7.07 (t, 1H, J=1.6 Hz), 6.94 (dd, 1H, J=1.2, 8.0 Hz), 4.12 (c, 2H, J=7.2 Hz), 3.75 (s, 2H), 2.89 (t, 2H, J=6.8 Hz), 2.60 (t, 2H, J=6.8 Hz), 2.29 (s, 3H), 1.24 (t, 1H, J=7.2 Hz).

Workup

  1. stirringAfter stirring for 3 hours
  2. customthe solvent was removed under vacuum
  3. customthe crude product was chromatographed over silica gel

Sources & evidence

ORD record
ord-f1d0e0115ac749e4bb4ecef23fbf46fc
Source dataset
uspto-grants-2005_03
Patent number
US06872730B2

Reaction notes

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