Potassium butoxide → HCID 69317316, compound

HRID 2115160Notes

Reaction equation

HRID 2115160 reaction equation
[O-][CH2:2]CCC.[K+].[CH:7]([CH:9]1[CH2:14][CH2:13][CH:12]([CH:15]2[CH2:20][CH2:19][CH:18]([C:21]3[CH:22]=[C:23]4[C:28](=[C:29]([F:31])[CH:30]=3)[O:27][C:26](=[O:32])[CH2:25][CH2:24]4)[CH2:17][CH2:16]2)[CH2:11][CH2:10]1)=O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[F:31][C:29]1[CH:30]=[C:21]([CH:18]2[CH2:17][CH2:16][CH:15]([CH:12]3[CH2:11][CH2:10][CH:9]([CH:7]=[CH2:2])[CH2:14][CH2:13]3)[CH2:20][CH2:19]2)[CH:22]=[C:23]2[C:28]=1[O:27][C:26](=[O:32])[CH2:25][CH2:24]2

Participants

5

Reactant 2

HCID 23699084Potassium butoxideHCID 86605567HCID 86605567, compound

Product 1

HCID 69317316HCID 69317316, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-30 °C

Procedure

Methyltriphenylphosphonium bromide (3.5 g) was suspended in THF (30 ml), to which was then added potassium butoxide (1.2 g) with stirring while cooling at −30° C. After continuing the stirring at the same temperature for 30 minutes, a solution of 6-(4-(4-formylcyclohexyl)cyclohexyl)-8-fluoro-3,4-dihydrocoumarin (3.2 g) in THF (30 ml) was added dropwise to the reaction mixture. After completion of the dropwise addition, the temperature of the reaction mixture was raised to room temperature, and the resulting reaction mixture was added in ice water and extracted with toluene. An organic layer was washed with water, dried over anhydrous magnesium sulfate, and then concentrated in vacuo. The resulting oily material was subjected to isolation and purification by silica gel column chromatography and recrystallized, thereby obtaining a titled compound (2.1 g).

Workup

  1. customfor 30 minutes
  2. additionAfter completion of the dropwise addition
  3. temperaturethe temperature of the reaction mixture was raised to room temperature
  4. customthe resulting reaction mixture
  5. extractionextracted with toluene
  6. washAn organic layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe resulting oily material was subjected to isolation and purification by silica gel column chromatography
  10. customrecrystallized

Sources & evidence

ORD record
ord-65b4622c2e274d53a23db2578152919a
Source dataset
uspto-grants-2008_10
Patent number
US07435455B2

Reaction notes

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