Water → Ethyl 4-cycloheptylidene-2-butenoate

HRID 844423Notes

Reaction equation

HRID 844423 reaction equation
C(OP([CH2:9][CH:10]=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[H-].[Na+].[C:19]1(=O)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.O>C(COC)OC>[C:19]1(=[CH:9][CH:10]=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

6

Reactant 4

HCID 962WaterHCID 10400CycloheptanoneHCID 24758Sodium hydrideHCID 264997ethyl (2E)-4-(diethoxyphosphoryl)but-2-enoate

Product 1

HCID 85420019Ethyl 4-cycloheptylidene-2-butenoate

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
10 °C

Procedure

6.7 ml of ethyl 4-(diethoxyphosphoryl)-2-butenoate are dissolved in 7 ml of dimethoxyethane and the solution is then poured onto 1.3 g of 60% sodium hydride in 40 ml of dimethoxyethane. After stirring for 45 minutes, the mixture is cooled to 10° C., 3.2 ml of cycloheptanone are then added dropwise and the mixture is allowed to return to RT. After stirring for 4 hours, the mixture is poured onto cold water and then extracted with ether, and the extracts are dried and evaporated. The residue is chromatographed on silica, eluting with DCM. 1.9 g of the expected compound are obtained.

Workup

  1. customto return to RT
  2. stirringAfter stirring for 4 hours
  3. extractionextracted with ether
  4. customthe extracts are dried
  5. customevaporated
  6. customThe residue is chromatographed on silica
  7. washeluting with DCM

Sources & evidence

ORD record
ord-3c09ec8876bf4ce9a33069488cf5ff7c
Source dataset
uspto-grants-2002_04
Patent number
US06380230B1

Reaction notes

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