1-Iodoheptane → 2-(2',3'-Difluoro-4'-heptylphenyl)-5-n-nonyl-1,3-dioxane

HRID 2292436Notes

Reaction equation

HRID 2292436 reaction equation
C([Li])CCC.[F:6][C:7]1[C:12]([F:13])=[CH:11][CH:10]=[CH:9][C:8]=1[CH:14]1[O:19][CH2:18][CH:17]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:16][O:15]1.I[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]>C1COCC1>[F:6][C:7]1[C:12]([F:13])=[C:11]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH:10]=[CH:9][C:8]=1[CH:14]1[O:15][CH2:16][CH:17]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:18][O:19]1

Participants

5

Reactant 3

HCID 202741-IodoheptaneHCID 214779412-(2',3'-Difluorophenyl)-5-n-nonyl-1,3-dioxaneHCID 178418339Butyllithium

Product 1

HCID 214779692-(2',3'-Difluoro-4'-heptylphenyl)-5-n-nonyl-1,3-dioxane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

n-Butyllithium (3.4 cm3, 10.0M in hexanes, 34mmol) was added dropwise to a stirred, cooled (-78° C.) solution of compound from Example 115 (mixture with isomers) (11.2 g, 34 mmol) in dry THF (100 cm3) under an atmosphere of dry nitrogen. The mixture was maintained under these conditions (3 h) then a solution of 1-iodoheptane (7.7 g, 34 mmol) in dry THF (20 cm3) was added dropwise at -78° C. The temperature of the reaction mixture was allowed to reach room temperature overnight. After separation, the aqueous layer was extracted with diethyl ether (2×150 cm3), the combined ethereal layers washed with water (2×150 cm3) and dried (MgSO4). The solvent was removed in vacuo to give the product as a brown oil which was purified by distillation under reduced pressure and recrystallised several times from methanol to remove the cis-isomer.

Workup

  1. temperatureThe mixture was maintained under these conditions (3 h)
  2. customAfter separation
  3. extractionthe aqueous layer was extracted with diethyl ether (2×150 cm3)
  4. washthe combined ethereal layers washed with water (2×150 cm3)
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-d888160e544044d2aaad9ec4a533bf2f
Source dataset
uspto-grants-1997_11
Patent number
US05683623

Reaction notes

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