Diethyl Ether → HCID 12960832, compound

HRID 224262Notes

Reaction equation

HRID 224262 reaction equation
[Cl-].[CH3:2][C:3]1[S:7][C:6]([CH3:8])=[C:5]([CH3:9])[C:4]=1[CH2:10][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C([Li])CCC.[F:35]/[C:36](=[C:42](/[CH:44]=O)\[CH3:43])/[C:37]([O:39][CH2:40][CH3:41])=[O:38].CCOCC>O1CCCC1.O>[F:35]/[C:36](=[C:42](\[CH3:44])/[CH:43]=[CH:10]/[C:4]1[C:5]([CH3:9])=[C:6]([CH3:8])[S:7][C:3]=1[CH3:2])/[C:37]([O:39][CH2:40][CH3:41])=[O:38]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 12960828HCID 12960828, compoundHCID 20494866HCID 20494866, compoundHCID 178418339Butyllithium

Product 1

HCID 12960832HCID 12960832, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-60 °C

Procedure

A suspension of 21.0 g. (48 mmol) of (2,4,5-trimethyl-3-thenyl)-triphenylphosphonium chloride in tetrahydrofuran was stirred under argon while being cooled to -60° C. The ylide was formed by adding 1.1 equivalents of n-butyllithium and warming to -35° C. for 15 minutes. A solution of 7.7 g. (48 mmol) of ethyl 2E-2-fluoro-3-formyl-2-butenoate in 50 ml. of anhydrous ether was added slowly. This mixture was warmed to 0° C., poured into water, extracted with hexane, washed twice with 60% methanol/water, water, saturated sodium chloride solution, dried and evaporated. Purification by silica gel chromatography gave 8.8 g. (58% yield) of ethyl (2E,4E)-2-fluoro-3-methyl-5-(2,4,5-trimethyl-3-thienyl)-2,4-pentadienoate.

Workup

  1. additionA suspension of 21.0 g
  2. customThe ylide was formed
  3. temperaturewarming to -35° C. for 15 minutes
  4. temperatureThis mixture was warmed to 0° C.
  5. extractionextracted with hexane
  6. washwashed twice with 60% methanol/water, water, saturated sodium chloride solution
  7. customdried
  8. customevaporated
  9. customPurification by silica gel chromatography
  10. customgave 8.8 g

Sources & evidence

ORD record
ord-b96745dc954443feb012f7061dd84768
Source dataset
uspto-grants-1980_11
Patent number
US04231944

Reaction notes

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