Ethyl bromoacetate → HCID 67713780, compound

HRID 232541Notes

Reaction equation

HRID 232541 reaction equation
[H-].[Na+].[C:3]1([C:9]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([O:20][C:21](=[O:24])CBr)C.[CH2:25]1COCC1>>[C:12]1([CH:11]2[C:9](=[O:10])[CH:3]=[CH:8][C:7]([CH2:6][CH2:5][CH2:4][C:21]([OH:24])=[O:20])=[CH:25]2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 4

HCID 7748Ethyl bromoacetateHCID 8028Tetrahydrofuran2×HCID 99482-PhenylacetophenoneHCID 24758Sodium hydride

Product 1

HCID 67713780HCID 67713780, compound

Procedure

To a solution of 6.0 g of 60% sodium hydride in 150 ml of THF was added dropwise a solution of 29.4 g of deoxybenzoin in 150 ml THF. The mixture was stirred for 10 min., 16.8 ml of ethylbromoacetate was added dropwise, and the reaction was then heated at reflux under nitrogen overnight. The reaction was then partitioned between ether and 5% aqueous sodium bicarbonate, washed twice with ether dried over magnesium sulfate, filtered and concentrated to 41.08 g of a brown oil. The crude product was mixed with 200 ml of methanol, 30 ml of water and 10 ml of 50% sodium hydroxide and then heated to reflux under nitrogen overnight. After this time the reaction was concentrated, partitioned between water and ether, washed twice with ether and dried over magnesium sulfate. The ether extracts were then concentrated and the residue triturated with cold ether to afford 6.45 gms of a yellow solid, mp 137°-139° C.

Workup

  1. temperaturethe reaction was then heated
  2. temperatureat reflux under nitrogen overnight
  3. customThe reaction was then partitioned between ether and 5% aqueous sodium bicarbonate
  4. washwashed twice with ether
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to 41.08 g of a brown oil
  8. additionThe crude product was mixed with 200 ml of methanol, 30 ml of water and 10 ml of 50% sodium hydroxide
  9. temperatureheated
  10. temperatureto reflux under nitrogen overnight
  11. concentrationAfter this time the reaction was concentrated
  12. custompartitioned between water and ether
  13. washwashed twice with ether
  14. dry with materialdried over magnesium sulfate
  15. concentrationThe ether extracts were then concentrated
  16. customthe residue triturated with cold ether

Sources & evidence

ORD record
ord-664b5ff32b074601bff2083593e74267
Source dataset
uspto-grants-1997_01
Patent number
US05591729

Reaction notes

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