Tetrabutylammonium Fluoride → HCID 10535231, compound

HRID 376284Notes

Reaction equation

HRID 376284 reaction equation
C(OC([N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][O:20]COCC[Si](C)(C)C)[N:14]=1)=O)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.CN(C)P(N(C)C)(N(C)C)=O>[NH:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[C:13]1[N:14]=[C:15]([CH2:19][OH:20])[CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 53679030HCID 53679030, compound

Product 1

HCID 10535231HCID 10535231, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
45 °C

Procedure

3 g of 2-[6-(2-trimethylsilanyl-ethoxymethoxy-methyl)pyridin-2-yl]pyrrole-1-carboxylic acid tert-butyl ester (7.41 mmol) are added to a solution of 3 ml of 1.1 M tetrabutylammonium fluoride in tetrahydrofuran, 45 ml of tetrahydrofuran and 5 ml of hexamethylphosphoramide, containing 10 g of molecular sieve (4 angstrom). The mixture is stirred at 45° C. under argon for 8 hours. After filtration of the insoluble matter on celite, the tetrahydrofuran is evaporated off. The title product is purified by chromatography on a silica column (eluent: dichloromethane/ethyl acetate; 99:1). 0.50 g of a white solid is recovered.

Workup

  1. additioncontaining 10 g of molecular sieve (4 angstrom)
  2. filtrationAfter filtration of the insoluble matter on celite
  3. customthe tetrahydrofuran is evaporated off
  4. customThe title product is purified by chromatography on a silica column (eluent: dichloromethane/ethyl acetate; 99:1)
  5. custom0.50 g of a white solid is recovered

Sources & evidence

ORD record
ord-aac1c4e7c53447c399817852c40b5d7d
Source dataset
uspto-grants-2000_02
Patent number
US06020345

Reaction notes

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