Water → HCID 13937660, compound

HRID 2118766Notes

Reaction equation

HRID 2118766 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.O=[C:7]1[CH2:15][C@@H:14]2[C@@H:9]([CH2:10][CH:11]=[CH:12][CH2:13]2)[CH2:8]1.[H-].[Na+].[OH2:18]>>[CH2:2]([O:1][C:5]([CH:4]=[C:7]1[CH2:15][C@@H:14]2[C@@H:9]([CH2:10][CH:11]=[CH:12][CH2:13]2)[CH2:8]1)=[O:18])[CH3:3]

Participants

5

Reactant 4

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 11116124HCID 11116124, compound

Product 1

HCID 13937660HCID 13937660, compound

Procedure

A tetrahydrofuran solution (100 ml) of 8-oxo-cis-bicyclo[4,3,0]nona-3-ene (80g) was added to a tetrahydrofuran solution (1000 ml) of the ylide prepared with triethyl phosphonoacetate (160 g) and sodium hydride (60% mineral oil dispersion, 23.5 g). The mixture was stirred for 30 min. at room temperature and poured into water and then extracted with ethylacetate. The organic layer was washed with water, dried, concentrated under reduced pressure to give 8-ethoxycarbonylmethylene-cis-bicyclo[4,3,0]nona-3-ene.

Workup

  1. extractionextracted with ethylacetate
  2. washThe organic layer was washed with water
  3. customdried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-beee09d722894b4187a9263648cbca04
Source dataset
uspto-grants-1987_07
Patent number
US04680307

Reaction notes

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