Diethyl Ether → HCID 12960838, compound

HRID 426698Notes

Reaction equation

HRID 426698 reaction equation
[Br-].[CH3:2][C:3]1[O:4][C:5]([CH3:28])=[C:6]([CH3:27])[C:7]=1[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH2:29]([Li])CCC.[F:34]/[C:35](=[C:41](\[CH:43]=O)/[CH3:42])/[C:36]([O:38][CH2:39][CH3:40])=[O:37].CCOCC>O1CCCC1.O>[F:34]/[C:35](=[C:41](/[CH3:42])\[CH:43]=[CH:29]\[C:7]1[C:6]([CH3:27])=[C:5]([CH3:28])[O:4][C:3]=1[CH3:2])/[C:36]([O:38][CH2:39][CH3:40])=[O:37]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 12960827HCID 12960827, compoundHCID 86736669HCID 86736669, compoundHCID 178418339Butyllithium

Product 1

HCID 12960838HCID 12960838, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-60 °C

Procedure

A suspension of 35 g. (75 mmol) of 2,4,5-trimethyl-3-furyl-triphenylphosphonium bromide in tetrahydrofuran was stirred under argon and 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 10.6 g. (66 mmol) of ethyl 2Z-2-fluoro-3-formyl-butenoate in 50 ml. of ether was added slowly. After warming to 0° C., the reaction was poured into water and extracted with hexane. This was purified by partitioning between hexane and a 60% methanol/water solution. The hexane phase was washed with water, dried and partially evaporated. This solution containing ethyl 2Z,4E-2-fluoro-3-methyl-5-(2,4,5-trimethyl-3-furyl)pentadienoate was carried on to the next step without further purification.

Workup

  1. additionA suspension of 35 g
  2. customThe ylide was formed
  3. temperaturewarming to -35° C. for 15 minutes
  4. temperatureAfter warming to 0° C.
  5. extractionextracted with hexane
  6. customThis was purified
  7. customby partitioning between hexane
  8. washThe hexane phase was washed with water
  9. customdried
  10. custompartially evaporated
  11. additionThis solution containing ethyl 2Z,4E-2-fluoro-3-methyl-5-(2,4,5-trimethyl-3-furyl)pentadienoate
  12. customwas carried on to the next step without further purification

Sources & evidence

ORD record
ord-1f0850e42be949fe9b5ec2b74049fee8
Source dataset
uspto-grants-1979_10
Patent number
US04171318

Reaction notes

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