Potassium Carbonate → HCID 10106471, compound

HRID 2220294Notes

Reaction equation

HRID 2220294 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[SH:9].C(=O)([O-])[O-].[K+].[K+].[CH2:16]([O:18][CH:19]([O:22][CH2:23][CH3:24])[CH2:20]Br)[CH3:17]>CN(C)C=O.O>[CH2:16]([O:18][CH:19]([O:22][CH2:23][CH3:24])[CH2:20][S:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1])[CH3:17]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 23642ThioguaiacolHCID 74852Ethane, 2-bromo-1,1-diethoxy-

Product 1

HCID 10106471HCID 10106471, compoundYield 101.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 2-methoxybenzenethiol (10 g, 71.4 mmol) and potassium carbonate (20 g, 143 mmol) in dry N,N-dimethylformamide (100 mL) was added dropwise over 20 mins a solution of bromoacetaldehyde diethyl acetal (10.3 mL, 71.4 mmol) in dry N,N-dimethylformamide (50 mL). The resulting suspension was allowed to stir at room temperature for 45 mins before being diluted with water (500 mL) and extracted with hexane (200 mL). The organic phase was further extracted with brine (4×100 mL), with the resulting organic phase being dried (MgSO4) and the solvent removed in vacuo to give a pale yellow oil (18.6 g) which was ca 95% pure. This material was further purified by flash chromatography eluting silica gel with hexane:ether [10:1] to give a colourless oil (18 g, 98%). δH (300 MHz, CDCl3) 7.34 (1H, d, Ar), 7.2 (1H, m, Ar), 6.92-6.80 (2H, m, Ar), 4.62 (1H, t, J=7 Hz, CH(OEt)2), 3.85 (3H, s, OCH3), 3.70-3.42 (4H, m, OCH2CH3), 3.10 (2H, d, J=7 Hz, SCH2), 1.12 (6H, t, J=7 Hz, OCH2CH3).

Workup

  1. extractionextracted with hexane (200 mL)
  2. extractionThe organic phase was further extracted with brine (4×100 mL), with the resulting organic phase
  3. dry with materialbeing dried (MgSO4)
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-3e6909e5689849a9af6891e234e89603
Source dataset
uspto-grants-2008_08
Patent number
US07417064B2

Reaction notes

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