3-Methoxybenzyl chloride → HCID 68497112, compound

HRID 1944205Notes

Reaction equation

HRID 1944205 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][C:8]([CH3:14])([CH3:13])[NH:9][CH2:10]2)=[CH:5][C:4]=1[O:15][Si:16]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18].[CH3:26][O:27][C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][CH:35]=1)[CH2:31]Cl>CCO>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][C:8]([CH3:13])([CH3:14])[N:9]([CH2:31][C:30]3[CH:33]=[CH:34][CH:35]=[C:28]([O:27][CH3:26])[CH:29]=3)[CH2:10]2)=[CH:5][C:4]=1[O:15][Si:16]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:18])[CH3:19]

Participants

4

Reactant 2

HCID 699943-Methoxybenzyl chlorideHCID 68495874HCID 68495874, compound

Product 1

HCID 68497112HCID 68497112, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 225 (300 mg, 0.83 mmol), 3-methoxybenzyl chloride (0.13 ml, 0.91 mmol) and TEA (0.3 ml, 1.65 mmol) in EtOH (3 ml) was heated in the microwave at 130° C. for 1.5 h. The reaction mixture was concentrated in vacuo. The crude residue was dissolved in EtOAc (30 ml), washed with brine (20 ml), dried (MgSO4) and concentrated in vacuo. Purification (flashmaster: 20 g, 100% hex to 50% hex/50% EtOAc and then to 100% EtOAc) afforded the title compound (246 mg, 62%) as colourless oil. 1H NMR (270 MHz; CDCl3) 1.04 (18H, d, J=6.7 Hz, CH3CH), 1.12-1.22 (3H, m, 3×SiCHCH3), 1.17 (6H, s, 2×CH3), 2.65 (2H, s, CH2), 3.47 (2H, s, CH2), 3.64 (2H, s, CH2), 3.74 (3H, s, OCH3), 3.79 (3H, s, OCH3), 6.41 (1H, s, CH), 6.48 (1H, s, CH), 6.77 (1H, ddd, J=8.2, 2.2, 1.2 Hz, CH), 6.95-6.98 (2H, m, 2×CH), 7.22 (1H, t, J=8.2 Hz, CH). 13C NMR (67.5 MHz; CDCl3) 12.38 (CH), 17.49 (CH3), 23.26 (CH3), 42.28 (CH2), 49.64 (CH2), 52.11 (C), 53.22 (CH2), 54.72 (OCH3), 55.04 (OCH3), 111.42 (CH), 111.69 (CH), 113.77 (CH), 117.21 (CH), 120.56 (CH), 125.68 (C), 126.34 (C), 128.69 (CH), 142.09 (C), 142.89 (C), 148.66 (C), 159.15 (C). LC/MS (ES+) tr=4.54 min, m/z 484.83 (M++H). HRMS (ES+) calcd. for C29H46NO3Si (M++H) 484.3241, found 484.3242.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionThe crude residue was dissolved in EtOAc (30 ml)
  3. washwashed with brine (20 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customPurification (flashmaster

Sources & evidence

ORD record
ord-e706c5224078409abc6fc47e55d23c45
Source dataset
uspto-grants-2013_03
Patent number
US08394825B2

Reaction notes

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