Tetrabutylammonium Fluoride → 197915-34-7

HRID 356557Notes

Reaction equation

HRID 356557 reaction equation
C([Si](C)(C)[O:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2([CH2:36][CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[O:21][C:20](=[O:22])[C:19]([S:23][C:24]3[CH:29]=[C:28]([CH3:30])[CH:27]=[CH:26][C:25]=3[C:31]([CH3:34])([CH3:33])[CH3:32])=[C:18]([OH:35])[CH2:17]2)=[CH:12][CH:11]=1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:31]([C:25]1[CH:26]=[CH:27][C:28]([CH3:30])=[CH:29][C:24]=1[S:23][C:19]1[C:20](=[O:22])[O:21][C:16]([C:13]2[CH:14]=[CH:15][C:10]([O:9][CH2:8][CH2:7][OH:6])=[CH:11][CH:12]=2)([CH2:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH2:17][C:18]=1[OH:35])([CH3:34])([CH3:32])[CH3:33]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 54686146HCID 54686146, compound

Product 1

HCID 54682310197915-34-7

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Deprotection of 1.75 g (2.7 mmol) of 6-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-phenyl }-3-(2-tert-butyl-5-methyl-phenylsulfanyl)-4-hydroxy-6-phenethyl-5,6-dihydro-pyran-2-one (prepared in the paragraph above) was accomplished as described in General Method 8 using 5.4 mL (5.4 mmol) of 1M tetrabutylammonium fluoride and 10 mL of THF. Purification by silica gel chromatography, eluting with MeOH:(50% Hexane-50% CH2Cl2) (1:99 to 5:95) gave the title compound, m.p. 154°-156° C.

Workup

  1. customPurification by silica gel chromatography
  2. washeluting with MeOH

Sources & evidence

ORD record
ord-cfaf0fea47434492b6a1821461c311b1
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

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