Dimethylformamide → HCID 54180946, compound

HRID 1111289Notes

Reaction equation

HRID 1111289 reaction equation
O[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].C1(C)C=CC(S(OOC[C@@H:27]([O:30][CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][O:32]2)[CH2:28][CH3:29])(=O)=O)=CC=1.CN(C)[CH:40]=[O:41]>>[O:32]1[CH2:33][CH2:34][CH2:35][CH2:36][C@@H:31]1[O:30][CH2:27][CH2:28][CH2:29][CH2:40][O:41][C:11]1[CH:12]=[CH:2][CH:3]=[CH:4][C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8434EthylparabenHCID 24758Sodium hydrideHCID 86744434HCID 86744434, compound

Product 1

HCID 54180946HCID 54180946, compound

Procedure

5 g (0.030 mol) of ethyl 4-hydroxybenzoate was added to 1.6 g (0.033 mol) of 50% sodium hydride and 50 ml of dimethylformamide under stirring at room temperature. The mixture was stirred for 30 min. 9.9 g (0.030 mol) of (S)-2-tetrahydropyranyloxybutoxy p-toluenesulfonate was added thereto and the mixture was stirred at 80° C. for 10 h. Then, the mixture was poured into ice-water and extracted with ethyl acetate. The extract was washed with a 10% aqueous sodium hydroxide solution and then with a saturated aqueous common salt solution, dried and concentrated to obtain 8.8 g of the crude product.

Workup

  1. stirringThe mixture was stirred for 30 min
  2. stirringthe mixture was stirred at 80° C. for 10 h
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with a 10% aqueous sodium hydroxide solution
  5. customwith a saturated aqueous common salt solution, dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5c4597ba148448778af1aa29cd14f413
Source dataset
uspto-grants-1990_12
Patent number
US04980082

Reaction notes

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