Tetrahydrofuran → HCID 22046634, compound

HRID 1826142Notes

Reaction equation

HRID 1826142 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[OH:19][C:20]1[C:44]([O:45][CH3:46])=[CH:43][C:23]2[C:24](=O)[N:25]3[CH2:41][CH2:40][CH2:39][C@H:26]3[C@H:27](O)[N:28](C(OCC[Si](C)(C)C)=O)[C:22]=2[C:21]=1[O:47][CH3:48].C1C[O:52]CC1>CCOC(C)=O>[CH3:46][O:45][C:44]1[C:20]([OH:19])=[C:21]([O:47][CH3:48])[C:22]2[N:28]=[CH:27][CH:26]3[CH2:39][C:40](=[O:52])[CH2:41][N:25]3[CH2:24][C:23]=2[CH:43]=1

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 2724141Tetrabutylammonium FluorideHCID 69621483HCID 69621483, compound

Product 1

HCID 22046634HCID 22046634, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
35 °C

Procedure

A solution of TBAF in THF (4.3 mL of a 1N solution, 4.3 mmol) was added to a rapidly stirred solution of 129 (0.37 g, 0.9 mmol) in THF (10 mL) and the reaction mixture heated to 35° C. for 2 h. The reaction mixture was diluted with EtOAc (50 mL), dried over anhydrous MgSO4, filtered and removal of excess solvent by rotary evaporation under reduced pressure afforded the product as a brown oil (0.18 g, 0.7 mmol, 78%). H1 NMR (CDCl3) mixture of C11/C11′R/S carbinolamine methyl ethers δ 7.08 (s, 1H), 4.43 (d, 1H, J=8.79 Hz), 4.05-3.23 (m, 12H), 2.3-1.48 (m, 4H).

Workup

  1. dry with materialdried over anhydrous MgSO4
  2. filtrationfiltered
  3. customremoval of excess solvent
  4. customby rotary evaporation under reduced pressure

Sources & evidence

ORD record
ord-8b71dcb9d39448c893083f14ed0b732f
Source dataset
uspto-grants-2006_05
Patent number
US07049311B1

Reaction notes

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