Sodium hydride → Methyl 4-(3-thienylmethoxy)-2-(2-trimethylsilylethoxy)methoxybenzoate

HRID 322953Notes

Reaction equation

HRID 322953 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:13]=[C:12]([O:14][CH2:15][C:16]2[CH:20]=[CH:19][S:18][CH:17]=2)[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7].[CH3:21][Si:22]([CH3:29])([CH3:28])[CH2:23][CH2:24][O:25][CH2:26]Cl>CN(C)C=O>[S:18]1[CH:19]=[CH:20][C:16]([CH2:15][O:14][C:12]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:3][CH2:26][O:25][CH2:24][CH2:23][Si:22]([CH3:29])([CH3:28])[CH3:21])[CH:13]=2)=[CH:17]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 10611649Methyl 2-hydroxy-4-(3-thienylmethoxy)benzoate

Product 1

HCID 22010432Methyl 4-(3-thienylmethoxy)-2-(2-trimethylsilylethoxy)methoxybenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred suspension of sodium hydride (1.53 g; 60% w/v dispersion in mineral oil; 38.3 mmol) in dimethylformamide (100 mL) is treated, portionwise, with methyl 2-hydroxy-4-(3-thienylmethoxy)benzoate (8.44 g) and stirred for 40 minutes. The mixture is treated with 2-(trimethyl-silyl)ethoxymethyl chloride (6.39 g), in one portion, and stirred at ambient temperature for three hours. It is then evaporated to dryness and the resulting residue is partitioned between water (100 mL) and ethyl acetate (100 mL). The organic layer is washed with brine (150 mL), dried over magnesium sulphate, filtered and concentrated in vacuo, to give methyl 4-(3-thienylmethoxy)-2-(2-trimethylsilylethoxy)methoxybenzoate, in the form of a yellow oil.

Workup

  1. additionis treated
  2. customIt is then evaporated to dryness
  3. customthe resulting residue is partitioned between water (100 mL) and ethyl acetate (100 mL)
  4. washThe organic layer is washed with brine (150 mL)
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dbc5781d75564efebbde0691687b2e11
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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