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

HRID 1703457Notes

Reaction equation

HRID 1703457 reaction equation
[O-]CC.[Na+].C([S:8][CH:9]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]=[CH:10]1)(=O)C.[CH2:16]([O:18][CH:19]([O:22][CH2:23][CH3:24])[CH2:20]Br)[CH3:17]>C(O)C>[CH2:16]([O:18][CH:19]([O:22][CH2:23][CH3:24])[CH2:20][S:8][CH:9]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]=[CH:10]1)[CH3:17]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of fresh sodium ethoxide prepared from 7.6 g (washed well 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 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. washwashed well gram-atom metallic sodium) in 200 ml of absolute ethanol
  2. temperatureThe reaction was heated
  3. temperatureunder reflux for 15 minutes
  4. temperatureThe reaction mixture was heated
  5. temperatureunder reflux for 2.0 hours
  6. temperaturecooled
  7. filtrationThe precipitated sodium bromide was filtered
  8. washwashed with absolute ethanol
  9. concentrationThe filtrate was concentrated
  10. customthe residue partitioned between ether/brine
  11. extractionThe aqueous phase was further extracted with ether
  12. dry with materialdried over magnesium sulfate
  13. customevaporated

Sources & evidence

ORD record
ord-c79ac81bf6ac4338b7150d6723fcd206
Source dataset
uspto-grants-1978_11
Patent number
US04124595

Reaction notes

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