Tetrahydrofuran → HCID 178444448、化合物

HRID 1590519ノート

反応式

HRID 1590519 の反応式
[Br-].[O:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:11][CH:10]=1.[CH2:37]([C@H:42]1[CH2:47][CH2:46][C@H:45]([CH:48]=O)[CH2:44][CH2:43]1)[CH2:38][CH2:39][CH2:40][CH3:41].O1CCCC1>O>[O:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][CH:17]=[CH:48][C@H:45]2[CH2:46][CH2:47][C@H:42]([CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[CH2:43][CH2:44]2)=[CH:13][CH:14]=1

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 18471791[3-(4-[2-Tetrahydropyranyloxy]phenyl)propyl]triphenylphosphonium bromideHCID 178444538HCID 178444538、化合物

生成物 1

HCID 178444448HCID 178444448、化合物収率 36.5%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of 4.0 g of [3-(4-[tetrahydro-2-pyranyloxy]phenyl)-1-propyl]triphenylphosphonium bromide, 1.3 g of trans-4-pentylcyclohexanecarboxaldehyde and 50 ml of absolute tetrahydrofuran was treated portionwise with 0.8 g of solid potassium t-butylate. After completion of the addition the reaction mixture was stirred for a further two hours and then poured into 500 ml of water and extracted three times with 100 ml of diethyl ether each time. The organic phases were washed twice with 500 ml of concentrated sodium chloride solution each time, dried over magnesium sulphate, filtered and subsequently concentrated. Chromatography of the residue on silica gel with toluene gave 1.0 g of 1-[tetrahydro-2-pyranyloxy]-4-[4-(trans-4-pentylcyclohexyl)-3-butenyl]benzene (cis/trans mixture).

後処理

  1. additionAfter completion of the addition the reaction mixture
  2. extractionextracted three times with 100 ml of diethyl ether each time
  3. washThe organic phases were washed twice with 500 ml of concentrated sodium chloride solution each time
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationsubsequently concentrated

出典と根拠

ORDレコード
ord-d792382d78724dcfb04306b60684f429
出典データセット
uspto-grants-1993_04
特許番号
US05204018

反応ノート

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