Diketene → HCID 14988341, compound

HRID 1087149Notes

Reaction equation

HRID 1087149 reaction equation
[CH2:1]([O:3][CH:4]([O:6][C:7]1[CH:16]=[CH:15][C:10](/[CH:11]=[CH:12]/[CH2:13][OH:14])=[CH:9][CH:8]=1)[CH3:5])[CH3:2].[CH2:17]=[C:18]1[O:22][C:20](=[O:21])[CH2:19]1>C(N(CC)CC)C>[C:20]([O:14][CH2:13]/[CH:12]=[CH:11]/[C:10]1[CH:9]=[CH:8][C:7]([O:6][CH:4]([O:3][CH2:1][CH3:2])[CH3:5])=[CH:16][CH:15]=1)(=[O:21])[CH2:19][C:18]([CH3:17])=[O:22]

Participants

4

Reactant 2

HCID 12661DiketeneHCID 14988336HCID 14988336, compound

Product 1

HCID 14988341HCID 14988341, compoundYield 70.9%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 9 g of 4(E)-(1-ethoxyethoxy)-cinnamyl alcohol and 0.5 ml of triethylamine was heated at 70°-80° C., and 6 g of diketene was slowly added dropwise thereto. After the addition was finished, the reaction mixture was heated at 110°-120° C. for 30 minutes. After the reaction was completed, the solvent was removed by evaporation under a reduced pressure, and the residue thus obtained was purified by means of a silica gel column chromatography (eluent: diethyl ether: n-hexane=1:3) to yield 8.8 g of 4(E)-(1-ethoxyethoxy)cinnamyl acetoacetate. Refractive index: D24 1.5305

Workup

  1. temperaturewas heated at 70°-80° C.
  2. additionAfter the addition
  3. temperaturethe reaction mixture was heated at 110°-120° C. for 30 minutes
  4. customthe solvent was removed by evaporation under a reduced pressure
  5. customthe residue thus obtained
  6. customwas purified by means of a silica gel column chromatography (eluent: diethyl ether: n-hexane=1:3)

Sources & evidence

ORD record
ord-4987e3f6edae4cb2a7e3bf3f7c597f49
Source dataset
uspto-grants-1991_07
Patent number
US05034395

Reaction notes

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