Furan, 2,5-dihydro-2,5-dimethoxy-2,5-dimethyl- → HCID 21569153, compound

HRID 1579692Notes

Reaction equation

HRID 1579692 reaction equation
CO[C:3]1([CH3:11])[CH:7]=[CH:6][C:5]([O:9]C)([CH3:8])[O:4]1.CC(=O)/C=C\C(=O)C.[C:20](O)(=[S:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(O)(=O)C.O>[C:20]([CH:6]([CH2:7][C:3](=[O:4])[CH3:11])[C:5](=[O:9])[CH3:8])(=[S:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 86653Furan, 2,5-dihydro-2,5-dimethoxy-2,5-dimethyl-HCID 535448517559-81-8HCID 178526132HCID 178526132, compound

Product 1

HCID 21569153HCID 21569153, compoundYield 69.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 962WaterSolvent

Procedure

In a 50 ml three-necked flask equipped with thermometer, 10 ml addition funnel and magnetic stirrer is placed 6 g of 2,5-dimethoxy-2,5-dimethyl-2,5-dihydrofuran, 24 ml H2O and 1 drop of glacial acetic acid. The mixture (which is crude cis-3-hexene-2,5-dione) is stirred for one hour until homogeneous. Then 5.25 g thiobenzoic acid is added over a five-minute period. The mixture is allowed to stand for eighteen more minutes and is then extracted with 35 ml of methylene chloride. After drying over anhydrous sodium sulfate and subsequent solvent removal, 7.55 g of crude 3-thiobenzoyl-2,5-hexanedione is recovered. The crude material is purified by column chromatography on 108 g silicic acid packed in ether:hexane (1:9) mixture. Elution with 630 ml ether:hexane (1:9) solvent mixture; followed by elution with 500 ml ether:hexane (1:4) solvent mixture; followed by elution with 850 ml ether:hexane (1:3) solvent mixture gives 6.2 g of 3-thiobenzoyl-2,5-hexanedione, having the following analyses:

Workup

  1. customIn a 50 ml three-necked flask equipped with thermometer, 10 ml addition funnel and magnetic stirrer
  2. extractionis then extracted with 35 ml of methylene chloride
  3. dry with materialAfter drying over anhydrous sodium sulfate and subsequent solvent removal, 7.55 g of crude 3-thiobenzoyl-2,5-hexanedione
  4. customis recovered
  5. customThe crude material is purified by column chromatography on 108 g silicic acid
  6. washElution with 630 ml ether:hexane (1:9) solvent mixture
  7. washfollowed by elution with 500 ml ether:hexane (1:4) solvent mixture
  8. washfollowed by elution with 850 ml ether:hexane (1:3) solvent mixture

Sources & evidence

ORD record
ord-5cfd7788792044c3b201809461b4d32f
Source dataset
uspto-grants-1976_01
Patent number
US03931270

Reaction notes

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