Potassium Carbonate → HCID 58415336, compound

HRID 2075160Notes

Reaction equation

HRID 2075160 reaction equation
[C:1]1([S:7][C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:15]([O:17][CH:18]([O:21][CH2:22][CH3:23])[CH2:19]Br)[CH3:16].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH2:15]([O:17][CH:18]([O:21][CH2:22][CH3:23])[CH2:19][O:14][C:11]1[CH:12]=[CH:13][C:8]([S:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:9][CH:10]=1)[CH3:16]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 113101954-(phenylthio)phenol

Product 1

HCID 58415336HCID 58415336, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(phenylthio)phenol (4.7 g, 23 mmol), bromoacetaldehyde diethyl acetal (4.3 mL, 28 mmol) and K2CO3 (3.82 g, 28 mmol) in DMF (40 mL) was stirred at reflux for 6 h. The reaction mixture was allowed to cool down to room temperature and poured over ice and diluted to 100 mL with water. The solution was extracted with Et2O (20 mL×3); the combined extracts were washed with 1N NaOH solution, water and brine, dried, and concentrated under reduced pressure to yield a yellow oil that was used without further purification: 1H NMR (400 MHz, CDCl3) δ 7.42 (d, 2H), 7.27-7.06 (m, 5H), 6.92 (d, 2H), 4.84 (t, 1H), 4.02 (d, 2H), 3.84-3.68 (m, 4H), 1.13 (m, 6H).

Workup

  1. temperatureat reflux for 6 h
  2. additionpoured over ice
  3. extractionThe solution was extracted with Et2O (20 mL×3)
  4. washthe combined extracts were washed with 1N NaOH solution, water and brine
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customto yield a yellow oil that
  8. customwas used without further purification

Sources & evidence

ORD record
ord-e49820e5865a4d05bd9ed6135f3c2226
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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