1-(Chloromethoxy)-2-methoxyethane → HCID 67087130, compound

HRID 2365569Notes

Reaction equation

HRID 2365569 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]2[CH:7]=[CH:8][N:9]([CH2:14][CH2:15][OH:16])[C:10]=2[CH:11]=[CH:12][CH:13]=1)=[O:4].CCN(C(C)C)C(C)C.Cl[CH2:27][O:28][CH2:29][CH2:30][O:31][CH3:32]>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[C:6]2[CH:7]=[CH:8][N:9]([CH2:14][CH2:15][O:16][CH2:27][O:28][CH2:29][CH2:30][O:31][CH3:32])[C:10]=2[CH:11]=[CH:12][CH:13]=1)=[O:4]

Participants

5

Reactant 3

HCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 81531DiisopropylethylamineHCID 67086833HCID 67086833, compound

Product 1

HCID 67087130HCID 67087130, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of -(2-Hydroxy-ethyl)-1H-indole-4-carboxylic acid methyl ester in DCM (3 ml) is added DIPEA (0.129 ml, 0.739 mmol) and 1-Chloromethoxy-2-methoxy-ethane (0.084 ml, 0.739 mmol). The solution is stirred at room temperature for 72 hours. The reaction is diluted with DCM (50 ml) and washed with 0.5 M HCl (20 ml), 1 M NaOH (20 ml) and 0.5 M HCl (20 ml). The organic layer is dried over MgSO4 and the solvent is removed in vacuo. Purification by chromatography (SiO2, DCM/MeOH) affords 1-[2-(2-Methoxy-ethoxymethoxy)-ethyl]-1H-indole-4-carboxylic acid methyl ester; [M+H]+ 308

Workup

  1. washwashed with 0.5 M HCl (20 ml), 1 M NaOH (20 ml) and 0.5 M HCl (20 ml)
  2. dry with materialThe organic layer is dried over MgSO4
  3. customthe solvent is removed in vacuo
  4. customPurification by chromatography (SiO2, DCM/MeOH)

Sources & evidence

ORD record
ord-48ea8fc3991b45fc954d1733b552d85b
Source dataset
uspto-grants-2014_04
Patent number
US08697687B2

Reaction notes

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