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Triethylamine → HCID 59463439, compound

HRID 1712979
Notes
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Reaction equation

HRID 1712979 reaction equation
[OH:1][CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]([O-:10])=[O:9])[CH:4]=1.[CH3:11][C:12]([Si:15](Cl)([CH3:17])[CH3:16])([CH3:14])[CH3:13].[CH3:19][CH2:20]N(CC)CC>CN(C=O)C.CCOC(C)=O>[CH2:19]([O:9][C:8]([C:5]1[CH:4]=[C:3]([CH2:2][O:1][Si:15]([C:12]([CH3:14])([CH3:13])[CH3:11])([CH3:17])[CH3:16])[O:7][N:6]=1)=[O:10])[CH3:20]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 8027248HCID 8027248, compound

Product 1

HCID 59463439HCID 59463439, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl Acetate
Solvent

Procedure

To a solution of 5-(hydroxymethyl)isoxazole-3-carboxylate (4.0 g, 23 mmol) and TBSCL (3.7 g, 25 mmol) in DMF is added Et3N (3.4 mL, 24 mmol) dropwise over 20 minutes. The reaction is allowed to stir for 30 minutes after which it is diluted with EtOAc (300 mL), washed with 1 M HCl (3×100 mL), 5% CuSO4 (2×50 mL) and concentrated in vacuo to yield ethyl-5-({[tert-butyl(dimethylsilyl)]oxy}methyl)isoxazole-3-carboxylate as an oily material.

Workup

  1. washwashed with 1 M HCl (3×100 mL), 5% CuSO4 (2×50 mL)
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-78903771c6be42af976af599c77e5929
Source dataset
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07795254B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes