Tetrabutylammonium Fluoride → HCID 18972191, compound

HRID 726814Notes

Reaction equation

HRID 726814 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, compound

Product 1

HCID 18972191HCID 18972191, compoundYield 99%

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-butyldimethylilyloxy-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-11f0202f4f7c4940ab11e30b377a6aec
Source dataset
uspto-grants-1998_01
Patent number
US05710288

Reaction notes

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