Methoxymethyl-triphenylphosphonium chloride → HCID 178495003、化合物

HRID 653372

反応式

HRID 653372 の反応式
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[C:24]([C:26]1[CH:31]=[CH:30][C:29]([C@H:32]2[CH2:37][CH2:36][C@H:35]([CH2:38][CH:39]=O)[CH2:34][CH2:33]2)=[CH:28][CH:27]=1)#[N:25]>COC(C)(C)C.O1CCCC1>[CH3:2][O:3][CH:4]=[CH:39][CH2:38][C@H:35]1[CH2:34][CH2:33][C@H:32]([C:29]2[CH:28]=[CH:27][C:26]([C:24]#[N:25])=[CH:31][CH:30]=2)[CH2:37][CH2:36]1

参加物

5

反応物 2

HCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 178509798HCID 178509798、化合物

生成物 1

HCID 178495003HCID 178495003、化合物収率 96%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 15413tert-Butyl methyl ether溶媒

反応条件

温度
0 °C

実験手順

A suspension of 22.2 g of methoxymethyl-triphenylphosphonium chloride in 150 ml of t-butyl methyl ether was treated with 7.4 g of solid potassium t-butylate at 0° C. within 3 minutes while gassing with argon in a sulphonation flask provided with a mechanical stirrer. The orange suspension was stirred at 0° C. for 1 hour and then treated dropwise within 10 minutes with a solution of 9.8 g of 2-[trans-4-(p-cyanophenyl)cyclohexyl]acetaldehyde in 100 ml of tetrahydrofuran. Subsequently, the suspension was left to warm slowly to room temperature while stirring. After 15 hours, the suspension was partitioned three times in diethyl ether/water. The organic extracts were washed twice with water, dried over magnesium sulphate, filtered and evaporated. In order to separate triphenylphosphine oxide, the residue was dissolved in ethyl acetate and the solution was diluted with petroleum ether, filtered and evaporated. Chromatographic separation of the resulting, yellowish oil (13.7 g) on silica gel with ethyl acetate/petroleum ether (vol. 5:95) gave 10.5 g (96%) of p-[trans-4-(3-methoxy-2-propenyl)cyclohexyl]benzonitrile as a colourless oil.

後処理

  1. customwhile gassing with argon in a sulphonation flask
  2. customprovided with a mechanical stirrer
  3. waitSubsequently, the suspension was left
  4. temperatureto warm slowly to room temperature
  5. stirringwhile stirring
  6. waitAfter 15 hours
  7. customthe suspension was partitioned three times in diethyl ether/water
  8. washThe organic extracts were washed twice with water
  9. dry with materialdried over magnesium sulphate
  10. filtrationfiltered
  11. customevaporated
  12. customIn order to separate triphenylphosphine oxide
  13. dissolutionthe residue was dissolved in ethyl acetate
  14. additionthe solution was diluted with petroleum ether
  15. filtrationfiltered
  16. customevaporated
  17. customChromatographic separation of the resulting, yellowish oil (13.7 g) on silica gel with ethyl acetate/petroleum ether (vol. 5:95)

出典と根拠

ORDレコード
ord-7f94ce98ec274b1c8d2c4bb4c23664d4
出典データセット
uspto-grants-1987_06
特許番号
US04676604

関連ノート

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