Water → HCID 14098167, compound

HRID 569271Notes

Reaction equation

HRID 569271 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH:5]1[CH2:13][C:12]2[C:7](=[C:8]([Cl:17])[C:9]([Cl:16])=[C:10]([O:14][CH3:15])[CH:11]=2)[C:6]1=[O:18].N12CCCC1=NCCC2.[CH:28]([C:30]([CH3:32])=[O:31])=[CH2:29].O>O1CCCC1>[Cl:1][CH2:2][CH2:3][CH2:4][C:5]1([CH2:29][CH2:28][C:30](=[O:31])[CH3:32])[CH2:13][C:12]2[C:7](=[C:8]([Cl:17])[C:9]([Cl:16])=[C:10]([O:14][CH3:15])[CH:11]=2)[C:6]1=[O:18]

Participants

6

Reactant 4

HCID 962WaterHCID 6570Methyl vinyl ketoneHCID 763491,5-Diazabicyclo(4.3.0)non-5-eneHCID 14098166HCID 14098166, compound

Product 1

HCID 14098167HCID 14098167, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(3-Chloropropyl)-6,7-dichloro-2,3-dihydro-5-methoxy-1H-inden-1-one (59 g, 0.20 mole) was dissolved in tetrahydrofuran (50 ml) and 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) (3 ml) added. The mixture was stirred and methyl vinyl ketone (28.3 g, 0.404 mole) added dropwise over 30 minutes. The temperature rose from 22° C. to 35° C. over the addition period. The mixture was stirred for an additional hour at ambient temperature, then poured into cold water. The solid that separated was removed by filtration, washed with water, dried and recrystallized from a mixture of tetrahydrofuran and ether to give 2-(3-chloropropyl)-6,7-dichloro-2,3-dihydro-5-methoxy-2-(3-oxobutyl)-1H-inden-1-one, 58.5 g, m.p. 120°-122° C.

Workup

  1. additionThe temperature rose from 22° C. to 35° C. over the addition period
  2. stirringThe mixture was stirred for an additional hour at ambient temperature
  3. customThe solid that separated
  4. customwas removed by filtration
  5. washwashed with water
  6. customdried
  7. customrecrystallized from a mixture of tetrahydrofuran and ether

Sources & evidence

ORD record
ord-329d619c6c1e40fbb6ce94397a5d5cff
Source dataset
uspto-grants-1988_03
Patent number
US04731470

Reaction notes

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