Tetrabutylammonium Fluoride → HCID 86742993, compound

HRID 1761768Notes

Reaction equation

HRID 1761768 reaction equation
[C:1]([O:4][CH2:5]/[CH:6]=[C:7](/[CH3:27])\[CH2:8][CH2:9]/[CH:10]=[C:11](\[CH3:26])/[CH2:12][CH2:13][CH:14]([O:18][Si](C(C)(C)C)(C)C)[C:15]([CH3:17])=[CH2:16])(=[O:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:1]([O:4][CH2:5]/[CH:6]=[C:7](/[CH3:27])\[CH2:8][CH2:9]/[CH:10]=[C:11](\[CH3:26])/[CH2:12][CH2:13][CH:14]([OH:18])[C:15]([CH3:17])=[CH2:16])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86742994HCID 86742994, compound

Product 1

HCID 86742993HCID 86742993, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The purified product obtained, (2Z,6E)-10-(tert.-butyldimethylsilyloxy)-3,7,11-trimethyl-2,6,11-dodecatrienyl acetate, is dissolved in 5 ml of tetrahydrofuran and treated with 320 mg of tetrabutylammonium fluoride. The solution is stirred at room temperature for 16 hours. After removing the solvent on a rotary evaporator the residue is chromatographed on silica gel with ether-hexane 1:1. There is obtained (2Z,6E)-10-hydroxy-3,7,11-trimethyl-2,6,11-dodecatrienyl acetate which exhibits the following bands in the IR spectrum: 3454 cm-1, 1739 cm-1, 1651 cm-1, 1446 cm-1, 1236 cm-1, 1023 cm-1, 955 cm-1, 898 cm-1.

Workup

  1. customThe purified product obtained
  2. customAfter removing the solvent
  3. customon a rotary evaporator the residue
  4. customis chromatographed on silica gel with ether-hexane 1:1

Sources & evidence

ORD record
ord-4be3a68100084ac19e1de3f2b3b13c3b
Source dataset
uspto-grants-1989_05
Patent number
US04827004

Reaction notes

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