Triethylamine → HCID 19006173, compound

HRID 1885147Notes

Reaction equation

HRID 1885147 reaction equation
[OH:1][CH2:2][C:3]1[S:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([Br:14])[CH:9]=2)=[CH:6][CH:7]=1.C(N(CC)CC)C.[C:22]([Si:26]([CH3:29])([CH3:28])Cl)([CH3:25])([CH3:24])[CH3:23]>C(Cl)Cl.C(OCC)(=O)C>[Si:26]([O:1][CH2:2][C:3]1[S:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([Br:14])[CH:9]=2)=[CH:6][CH:7]=1)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:29])[CH3:28]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 19006170HCID 19006170, compound

Product 1

HCID 19006173HCID 19006173, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-(hydroxymethyl)-5-(3'-bromophenyl)thiophene (1.08 G; 4 mM) and triethylamine (1.4 mL; 10 mM) in 20 ml of methylene chloride at R.T. was added t-butyldimethylchlorosilane (1.5 g; 10 mM). This mixture was stirred overnight, diluted with 30 ml of ethyl acetate, washed with 2×15 ml of sat'd. sodium chloride solution, and dried over anhyd. magnesium sulfate. Solvent was removed to give a residue, which was purified on silica gel with ether: petroleum ether (1:20) as solvent mixture. Eluate was distilled to give 0.99 g of 2-(t-butyldimethylsilyloxymethyl)-5-(3'bromophenyl)thiophene as colorless liquid boiling at 167°-170°/~0.2 mm.

Workup

  1. washwashed with 2×15 ml of sat'd
  2. dry with materialsodium chloride solution, and dried over anhyd
  3. customSolvent was removed
  4. customto give a residue, which
  5. customwas purified on silica gel with ether: petroleum ether (1:20) as solvent mixture
  6. distillationEluate was distilled

Sources & evidence

ORD record
ord-605946c9ccf24ec7948d1eda443cad54
Source dataset
uspto-grants-1992_09
Patent number
US05143914

Reaction notes

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