Water → HCID 86743858, compound

HRID 2073378Notes

Reaction equation

HRID 2073378 reaction equation
[Br-].[C:2]([CH2:4][CH2:5][CH2:6][CH2:7][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)#[N:3].CC(C)([O-])C.[K+].C(OC(N[C@@H:41]1[C@H:46]([CH2:47][CH:48]=O)[CH2:45][C@H:44]2[CH2:50][C@H:42]1[C:43]2([CH3:52])[CH3:51])=O)(C)(C)C.O>O1CCCC1>[C:2]([CH2:4][CH2:5][CH2:6]/[CH:7]=[CH:48]\[CH2:47][CH:46]1[CH2:41][CH:42]2[CH2:50][CH:44]([C:43]2([CH3:51])[CH3:52])[CH2:45]1)#[N:3]

Participants

6

Reactant 4

HCID 962WaterHCID 11418829(4-Cyanobutyl)(triphenyl)phosphanium bromideHCID 23665647Potassium tert-butoxideHCID 86743859HCID 86743859, compound

Product 1

HCID 86743858HCID 86743858, compoundYield 41.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 30.3 g of (4-cyanobutyl)triphenylphosphonium bromide in 140 ml of tetrahydrofuran is added 8.07 g of potassium-tert-butoxide under stirring in an nitrogen atmosphere and the mixture is stirred at room temperature for 1.5 hours. A solution of the above prepared crude aldehyde 3c in 50 ml of tetrahydrofuran is dropwise added at 0° C. and the resulting mixture is stirred at the same temperature for 1 hour. Water is added to the reaction mixture, then which is extracted with ether. The organic layer is washed with water, dried over anhydrous sodium sulfate, and evaporated under reduced pressure. The residue is purified by flash chromatography on 200 g of silica gel (hexane:ethyl acetate=6:1) to give 6.9 g of the titled compound 7a in 41.8% yield.

Workup

  1. stirringthe mixture is stirred at room temperature for 1.5 hours
  2. additionis dropwise added at 0° C.
  3. stirringthe resulting mixture is stirred at the same temperature for 1 hour
  4. extractionwhich is extracted with ether
  5. washThe organic layer is washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated under reduced pressure
  8. customThe residue is purified by flash chromatography on 200 g of silica gel (hexane:ethyl acetate=6:1)

Sources & evidence

ORD record
ord-d9dfeb2b846f47c8a06b4d7655420223
Source dataset
uspto-grants-1990_04
Patent number
US04916231

Reaction notes

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