Ethanol → HCID 11781486, compound

HRID 1936565Notes

Reaction equation

HRID 1936565 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][C:10]3=[CH:12][CH:13]=[CH:14][N:9]3[CH2:8][CH:7](O)[C:6]=2[CH:16]=1.P(Br)(Br)[Br:18].C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)C>[Br:18][CH:7]1[C:6]2[CH:16]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=2[S:11][C:10]2=[CH:12][CH:13]=[CH:14][N:9]2[CH2:8]1

Participants

6

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 24614Phosphorus tribromideHCID 10868268HCID 10868268, compound

Product 1

HCID 11781486HCID 11781486, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 24c (0.17 g 0.71 mmol) in dry ethyl ether (3 ml) was added dropwise a solution of phosphorus tribromide (μL 33.5, 0.36 mmol) in dry ethyl ether (0.7 ml); the reaction mixture was refluxed for 2 hours under argon atmosphere. After cooling to room temperature dry ethanol (μL 143) was added and the resulting solution was heated at reflux for 1 hour. Then 4 ml of aqueous sodium carbonate was added; the organic phase was separated, dried and evaporated. The crude product was chromatographed (50% petroleum ether 40-60° in dichloromethane) to give 0.103 g of pure 25c (48% yield). 1H NMR (CDCl3) δ7.35-7.16 (m, 2H); 6.92-6.82 (m, 2H); 6.39-6.37 (m, 1H); 6.13-6.09 (m, 1H); 5.69-5.64 (m, 1H); 5.10-5.01 (dd, 1H, J=14.57, 2.65 Hz); 4.70-4.59 (dd, 1H, J=14.88, 7.05 Hz).

Workup

  1. temperaturethe reaction mixture was refluxed for 2 hours under argon atmosphere
  2. additionwas added
  3. temperaturethe resulting solution was heated
  4. temperatureat reflux for 1 hour
  5. customthe organic phase was separated
  6. customdried
  7. customevaporated
  8. customThe crude product was chromatographed (50% petroleum ether 40-60° in dichloromethane)

Sources & evidence

ORD record
ord-202c85ef3f66410d8b8a0ae81a6a5d8a
Source dataset
uspto-grants-2002_05
Patent number
US06391870B2

Reaction notes

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