Tetrahydrofuran → HCID 178444448, compound

HRID 1590519Notes

Reaction equation

HRID 1590519 reaction equation
[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

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 18471791[3-(4-[2-Tetrahydropyranyloxy]phenyl)propyl]triphenylphosphonium bromideHCID 178444538HCID 178444538, compound

Product 1

HCID 178444448HCID 178444448, compoundYield 36.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-d792382d78724dcfb04306b60684f429
Source dataset
uspto-grants-1993_04
Patent number
US05204018

Reaction notes

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