Tetrabutylammonium Fluoride → HCID 18972191, compound

HRID 861690Notes

Reaction equation

HRID 861690 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH3:19][O:20][C:21](=[O:51])[CH2:22][CH2:23][CH2:24][CH2:25][CH:26]1[O:30][C:29]2[CH:31]=[C:32]([CH:35]([O:43][Si](C(C)(C)C)(C)C)[CH2:36][CH2:37][C:38]3[S:39][CH:40]=[CH:41][CH:42]=3)[CH:33]=[CH:34][C:28]=2[O:27]1>C1COCC1.CCOC(C)=O>[CH3:19][O:20][C:21](=[O:51])[CH2:22][CH2:23][CH2:24][CH2:25][CH:26]1[O:30][C:29]2[CH:31]=[C:32]([CH:35]([OH:43])[CH2:36][CH2:37][C:38]3[S:39][CH:40]=[CH:41][CH:42]=3)[CH:33]=[CH:34][C:28]=2[O:27]1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 54359124HCID 54359124, compound2×

Product 1

HCID 18972191HCID 18972191, compoundYield 99.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Tetrabutylammonium fluoride (0.58 mL of a 1.0M solution in THF, 0.58 mmol) was added to (±)-methyl-5-[[6-(1-t-butyldimethylsilyloxy-3-(2-thienyl)propyl)]-1,3-benzodioxolyl]pentanoate (Compound E, 178 mg, 0.36 mmol) in THF (4.5 mL). After 16 hours the reaction was diluted with EtOAc and washed with H2O. The organic portion was dried (MgSO4) filtered and concentrated in vacuo. Flash column chromatography (silica gel, 2:1 hex/EtOAc) gave 135 mg (99%) of the title compound. 1H NMR (300 MHz, CDCl3) δ 7.14 (d, J=5.1 Hz, 1H), 7.01 (s, 1H), 6.93 (dd, J=3.3, 5.1 Hz, 1H), 6.83 (d, J=3.3 Hz, 1H), 6.60 (s, 1H), 5.92 (s, 2H), 4.88-4.91 (m, 1H), 3.67 (s, 3H), 2.96-3.03 (m, 2H), 2.43-2.49 (m, 2H), 2.29 (t, J=6.9 Hz, 2H), 1.88-2.20 (m, 2H), 1.80 (d, J=3.0 Hz, 1H), 1.44-1.66 (m, 4H).

Workup

  1. washwashed with H2O
  2. dry with materialThe organic portion was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a2ead23597bf434a99f676a677fd779b
Source dataset
uspto-grants-1998_02
Patent number
US05714621

Reaction notes

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