Ethane, 2-bromo-1,1-diethoxy- → 3-[(2,2-Diethoxyethyl)sulfanyl]cyclohept-1-ene

HRID 903624Notes

Reaction equation

HRID 903624 reaction equation
[O-]CC.[Na+].[Na].C([S:9][CH:10]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]=[CH:11]1)(=O)C.[CH2:17]([O:19][CH:20]([O:23][CH2:24][CH3:25])[CH2:21]Br)[CH3:18]>C(O)C>[CH2:17]([O:19][CH:20]([O:23][CH2:24][CH3:25])[CH2:21][S:9][CH:10]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]=[CH:11]1)[CH3:18]

Participants

6

Reactant 4

HCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 126209593-Acetylmercaptocycloheptene

Product 1

HCID 126209603-[(2,2-Diethoxyethyl)sulfanyl]cyclohept-1-eneYield 99.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

A solution of fresh sodium ethoxide prepared from 7.6 g (0.330 gram-atom metallic sodium) in 200 ml of absolute ethanol was treated dropwise with 56.18 g (0.330 mole) of 3-acetylmercaptocycloheptene in 10 ml of absolute ethanol. The reaction was heated under reflux for 15 minutes and then cooled to room temperature. A solution of 49.69 ml (0.330 mole) of bromoacetaldehyde diethylacetal in 30 ml of absolute ethanol was added dropwise. The reaction mixture was heated under reflux for 2.0 hours and cooled. The precipitated sodium bromide was filtered and washed well with absolute ethanol. The filtrate was concentrated and the residue partitioned between ether/brine. The aqueous phase was further extracted with ether. The organic extracts were pooled, dried over magnesium sulfate, and evaporated to afford 80.1 g (0.328 mole, 99%) of pure 3-[(2,2-diethoxyethyl)thio]-1-cycloheptene, as a colorless oil.

Workup

  1. temperatureThe reaction was heated
  2. temperatureunder reflux for 15 minutes
  3. temperatureThe reaction mixture was heated
  4. temperatureunder reflux for 2.0 hours
  5. temperaturecooled
  6. filtrationThe precipitated sodium bromide was filtered
  7. washwashed well with absolute ethanol
  8. concentrationThe filtrate was concentrated
  9. customthe residue partitioned between ether/brine
  10. extractionThe aqueous phase was further extracted with ether
  11. dry with materialdried over magnesium sulfate
  12. customevaporated

Sources & evidence

ORD record
ord-c1b9c80d87e942b0a92b5cb2df3a8e82
Source dataset
uspto-grants-1980_10
Patent number
US04228295

Reaction notes

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