Tetrahydrofuran → HCID 53719390, compound

HRID 847285Notes

Reaction equation

HRID 847285 reaction equation
[Cl-].[C:2]1([CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:38]=[CH:37][C:16]([CH2:17][P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)=[C:15](OC)[CH:14]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.CCCCCC.[CH:52]([C:54]1[CH:66]=[CH:65][CH:64]=[CH:63][C:55]=1[O:56][CH2:57][C:58]([O:60][CH2:61][CH3:62])=[O:59])=O.[Cl-].[NH4+].[O:69]1CCC[CH2:70]1>>[CH3:70][O:69][C:38]1[CH:37]=[C:16]([CH:15]=[CH:14][C:13]=1[O:12][CH2:11][CH2:10][CH2:9][CH2:8][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH:17]=[CH:52][C:54]1[CH:66]=[CH:65][CH:64]=[CH:63][C:55]=1[O:56][CH2:57][C:58]([O:60][CH2:61][CH3:62])=[O:59]

Participants

6

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 345961ethyl 2-(2-formylphenoxy)acetateHCID 19882721HCID 19882721, compoundHCID 178418244HCID 178418244, compound

Product 1

HCID 53719390HCID 53719390, compound

Procedure

To a suspension of 260 mg of [4-(4-phenylbutoxy)-2-methoxybenzyl]triphenylphosphonium choride obtained in Reference Example 22 in 2.5 ml of tetrahydrofuran was dropwise added 0.36 ml of a 1.42M n-butyl lithium/hexane solution. The mixture was stirred for 10 minutes to form a dark red solution. The solution was dropwise added to a solution of 114 mg of ethyl o-formylphenoxyacetate in 1 ml of tetrahydrofuran at 0° C. using an injection tube. After stirring for 20 minutes, a saturated ammonium chloride aqueous solution was added thereto. The product was extracted with ether. After washing with water and then an aqueous saline solution, the ethereal layer was dried and concentrated. The crude product was fractionated and separated by TLC (developer; hexane:methylene chloride:acetone=8:2:1) to obtain 170 mg of ethyl o-[3-methoxy-4-(4-phenylbutoxy)styryl]phenoxyacetate.

Workup

  1. customto form a dark red solution
  2. stirringAfter stirring for 20 minutes
  3. extractionThe product was extracted with ether
  4. washAfter washing with water
  5. customan aqueous saline solution, the ethereal layer was dried
  6. concentrationconcentrated
  7. customseparated by TLC (developer; hexane:methylene chloride:acetone=8:2:1)

Sources & evidence

ORD record
ord-161ca126bcf34a4387d7b8260add50c4
Source dataset
uspto-grants-1992_08
Patent number
US05140046

Reaction notes

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