Tetrabutylammonium Fluoride → HCID 12017361, compound

HRID 1937054Notes

Reaction equation

HRID 1937054 reaction equation
C([Si]([O:18][CH2:19][CH2:20][CH2:21]/[CH:22]=[CH:23]/[CH:24]=[C:25](\[CH3:33])/[CH2:26][CH2:27][CH:28]1[O:32][CH2:31][CH2:30][O:29]1)(C1C=CC=CC=1)C1C=CC=CC=1)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[O:29]1[CH2:30][CH2:31][O:32][CH:28]1[CH2:27][CH2:26]/[C:25](/[CH3:33])=[CH:24]/[CH:23]=[CH:22]/[CH2:21][CH2:20][CH2:19][OH:18]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 12017362HCID 12017362, compound

Product 1

HCID 12017361HCID 12017361, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(4E,6E)-9-[1,3]Dioxolan-2-yl-7-methyl-nona-4,6-dien-1-ol was synthesized in the following manner. A solution of tert-butyl-(4E,6E)-(9-[1,3]dioxolan-2-yl-7-methyl-nona-4,6-dienyloxy)-diphenyl-silane (3.35 g, 7.28 mmol) in 75 mL of THF was cooled to 0° C. and treated dropwise with 10 mL of a 1 M solution of TBAF in THF. The reaction mixture was stirred at 0° C. to room temperature for 11 hours, quenched with a saturated NaHCO3 solution, extracted with Et2O, dried (Na2SO4), and concentrated. Purification of the residue by column chromatography on SiO2 (2:1 hexanes-EtOAc) provided 1.44 g (6.38 mmol, 88%) of oily (4E,6E)-9-[1,3]dioxolan-2-yl-7-methyl-nona-4,6-dien-1-ol: 1H NMR δ6.28 (dd, 1H, J=14.9, 10.9 Hz), 5.84 (d, 1H, J=10.7 Hz), 5.59 (dt, 1H, J=14.4, 7.0 Hz), 4.86 (t, 1H, J=4.7 Hz), 4.00-3.80 (m, 4H), 3.67 (t, 2H, J=6.5Hz) 2.50-2.38 (m, 1H), 2.25-2.10 (m, 4H), 1.80-1.75 (m, 2H), 1.75 (s, 3H), 1.68 (p, 2H, J=6.7 Hz).

Workup

  1. custom(4E,6E)-9-[1,3]Dioxolan-2-yl-7-methyl-nona-4,6-dien-1-ol was synthesized in the following manner
  2. customquenched with a saturated NaHCO3 solution
  3. extractionextracted with Et2O
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customPurification of the residue by column chromatography on SiO2 (2:1 hexanes-EtOAc)

Sources & evidence

ORD record
ord-78a5c4b6b464411cb3b42c48a77f2fb7
Source dataset
uspto-grants-2002_05
Patent number
US06392055B1

Reaction notes

Loading…