Tetrabutylammonium Fluoride → 2-[N-(methoxycarbonylmethyl)carbamoyl]-5-(3-thienylmethoxy)phenol

HRID 322950Notes

Reaction equation

HRID 322950 reaction equation
[CH3:1][O:2][C:3]([CH2:5][NH:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:21]=[CH:20][S:19][CH:18]=2)=[CH:11][C:10]=1[O:22]COCC[Si](C)(C)C)=[O:8])=[O:4].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:1][O:2][C:3]([CH2:5][NH:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:21]=[CH:20][S:19][CH:18]=2)=[CH:11][C:10]=1[OH:22])=[O:8])=[O:4]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 220102001-[N-(methoxycarbonylmethyl)carbamoyl]-2-[2-(trimethylsilyl)ethoxy]methoxy-4-(3-thienylmethoxy)benzene

Product 1

HCID 220105102-[N-(methoxycarbonylmethyl)carbamoyl]-5-(3-thienylmethoxy)phenolYield 97.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 1-[N-(methoxycarbonylmethyl)carbamoyl]-2-[2-(trimethylsilyl)ethoxy]methoxy-4-(3-thienylmethoxy)benzene (3.3 g), tetrabutylammonium fluoride (20 mL of a 1 M solution in tetrahydrofuran) and tetrahydrofuran (30 mL) is stirred at ambient temperature for one hour and at reflux for 45 minutes, then it is cooled to ambient temperature and concentrated in vacuo. The resulting residue is partitioned between ethyl acetate (100 mL) and saturated brine (100 mL), and the organic layer is washed with brine (2×50 mL), dried over magnesium sulphate, filtered and concentrated in vacuo. Flash chromatography of the residual oil on silica gel, eluting with a mixture of methanol and dichloromethane (2:98 v/v) gives 2-[N-(methoxycarbonylmethyl)carbamoyl]-5-(3-thienylmethoxy)phenol (2.3 g), in the form of a white solid.

Workup

  1. temperatureat reflux for 45 minutes
  2. temperatureit is cooled to ambient temperature
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue is partitioned between ethyl acetate (100 mL) and saturated brine (100 mL)
  5. washthe organic layer is washed with brine (2×50 mL)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. washFlash chromatography of the residual oil on silica gel, eluting with a mixture of methanol and dichloromethane (2:98 v/v)

Sources & evidence

ORD record
ord-b2acd811147a4171bcf88639e98fe8ee
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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