Water → HCID 68492920, compound

HRID 1944233Notes

Reaction equation

HRID 1944233 reaction equation
CO[C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5]Cl.[OH2:11].[C:12]([O:15][CH2:16][CH3:17])(=O)C.[CH3:18][N:19]([CH:21]=O)[CH3:20]>>[CH3:12][O:15][C:16]1[CH:17]=[CH:5][CH:4]=[CH:3][C:10]=1[CH2:21][N:19]1[CH2:18][CH2:5][C:4]2[C:7](=[CH:8][CH:9]=[C:10]([OH:11])[CH:3]=2)[CH2:20]1

Participants

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 814952-(Chloromethyl)anisole

Product 1

HCID 68492920HCID 68492920, compoundYield 85%

Conditions

Temperature
80 °C

Procedure

A solution of B1 (345 mg, 1.5 mmol), and 2-methoxybenzyl chloride (230 μL, 1.65 mmol) in DMF (10 mL) was treated with Huning's base (1.82 mL, 10.5 mmol) and heated to 80° C. for 60 h. After cooling to room temperature, water (5 mL) was added and the product extracted with ethyl acetate (4×10 mL). The combined organics were washed with water, brine and dried over MgSO4, prior to evaporation and purification by flash column chromatography. B16 was isolated as a white solid in 85% yield (345 mg). m.p. 148-155° C.; Rf: 0.23 (1:1 Petrol:ethyl acetate) 1H NMR (270 MHz, CDCl3) δ 2.66-2.70 (2H, m), 2.73-2.76 (2H, m), 3.59 (2H, br s), 3.74 (2H, br s), 3.75 (3H, s), 6.20 (1H, d, J=2.43), 6.39 (1H, dd, J=2.7, 9.2), 6.73 (1H, d, J=9.2) 6.83-6.92 (2H, m), 7.24 (1H, dt, J=1.6, 8.1), 7.36 (1H, dd, J=1.4, 8.1); HRMS (ES+) calcd. for C17H20NO2 (M++H) 270.1489, found 270.1478; LC/MS (ES+) tr=1.92 min, m/z 270.4 (M++H); HPLC tr=2.917 min (>98%).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe product extracted with ethyl acetate (4×10 mL)
  3. washThe combined organics were washed with water, brine
  4. dry with materialdried over MgSO4
  5. customto evaporation and purification by flash column chromatography
  6. customB16 was isolated as a white solid in 85% yield (345 mg)
  7. customLC/MS (ES+) tr=1.92 min, m/z 270.4 (M++H)
  8. customHPLC tr=2.917 min (>98%)

Sources & evidence

ORD record
ord-c5cda648dcf84fec8324a4f3e53db63f
Source dataset
uspto-grants-2013_03
Patent number
US08394825B2

Reaction notes

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