Diethyl Ether → HCID 86733882, compound

HRID 437901Notes

Reaction equation

HRID 437901 reaction equation
C([Li])CCC.[CH2:6]([Cl:8])Cl.C(OCC)C.[CH3:14][O:15][C:16]([CH:18]([C:23](=[O:25])[CH3:24])[CH2:19]/[CH:20]=[CH:21]\[CH3:22])=[CH2:17]>CCCCCC.O1CCCC1.C1(C)C=CC=CC=1>[Cl:8][CH:6]1[O:25][C:23]1([CH3:24])[CH:18]([C:16]([O:15][CH3:14])=[CH2:17])[CH2:19]/[CH:20]=[CH:21]\[CH3:22]

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 6344DichloromethaneHCID 86733881HCID 86733881, compoundHCID 178418339Butyllithium

Product 1

HCID 86733882HCID 86733882, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

A solution of 28 ml. (45 mmol.) of 1.6 M n-butyl lithium in hexane was added dropwise and with stirring during 45 minutes to a solution of 3.2 ml. (50 mmol.) of methylene chloride in 20 ml. of diethyl ether, 20 ml. of petroleum ether, and 140 ml. tetrahydrofuran under nitrogen cooled to -95° in a toluene-liquid nitrogen slush. After 30 minutes, a solution of 6.72 g. (40 mmol.) of (Z)-2-methoxy- 3-acetyl-1,5-heptadiene in 60 ml. of tetrahydrofuran was added dropwise during 45 minutes and the mixture was allowed to warm slowly to room temperature and then allowed to reflux for three hours. The mixture was then cooled, concentrated, poured into 200 ml. of saturated aqueous ammonium chloride, extracted with diethyl ether, the combined ethereal extracts washed with saturated aqueous sodium chloride, dried (Na2SO4) and concentrated to afford (Z)- 1-chloro-1,2-epoxy-2-methyl-3-(1-methoxyethenyl)-5-heptene.

Workup

  1. waitAfter 30 minutes
  2. temperatureto reflux for three hours
  3. temperatureThe mixture was then cooled
  4. concentrationconcentrated
  5. additionpoured into 200 ml
  6. extractionof saturated aqueous ammonium chloride, extracted with diethyl ether
  7. washthe combined ethereal extracts washed with saturated aqueous sodium chloride
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-cbe563c0faf3415d8813e70af764feb8
Source dataset
uspto-grants-1977_06
Patent number
US04032577

Reaction notes

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