Ethyl formate → HCID 23345434, compound

HRID 866540Notes

Reaction equation

HRID 866540 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C:10]2=[O:16])[CH:6]=[CH:7][CH:8]=1.[Na].[CH:24](OCC)=[O:25].C(OC(CC1CCCCC(C=O)C1=O)=O)C>CCOCC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]([CH:24]=[O:25])[C:10]2=[O:16])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 8025Ethyl formateHCID 5360545SodiumHCID 20319563HCID 20319563, compoundHCID 23345431HCID 23345431, compound

Product 1

HCID 23345434HCID 23345434, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture was prepared containing 313 g. of 2-(m-methoxyphenyl)-2-ethoxycarbonylmethyl-cycloheptanone, 2 liters of ether, 332.9 g. of sodium and 115.7 g. of ethyl formate. The reaction mixture was stirred at ambient temperature for 5 days and then poured onto an ice-water mixture. The ether layer was separated and saved for recovery of starting material. The aqueous layer was acidified with cold 10 percent aqueous hydrochloric acid and the resulting acidic layer extracted with an equal volume of ether. The ether extract was separated, washed three times with a saturated aqueous sodium chloride solution and then dried. Evaporation of the solvent yielded 243 g. of 2-m-methoxyphenyl)-2-ethoxycarbonylmethyl-7-formylcycloheptanone. Molecular ion by mass spectrograph 332.

Workup

  1. customA mixture was prepared
  2. additioncontaining 313 g
  3. customThe ether layer was separated
  4. extractionthe resulting acidic layer extracted with an equal volume of ether
  5. extractionThe ether extract
  6. customwas separated
  7. washwashed three times with a saturated aqueous sodium chloride solution
  8. customdried
  9. customEvaporation of the solvent
  10. customyielded 243 g

Sources & evidence

ORD record
ord-75c5f3d16fed47e8b745d0ff6ccbb38b
Source dataset
uspto-grants-1978_07
Patent number
US04100166

Reaction notes

Loading…