Benzaldehyde → HCID 22998524, compound

HRID 234444Notes

Reaction equation

HRID 234444 reaction equation
[Li]CCCC.[CH3:6][Si:7]([CH3:29])([CH3:28])[CH2:8][CH2:9][O:10][CH2:11][C:12]1[S:13][CH:14]=[CH:15][C:16]=1[S:17]([NH:20][C:21]1[O:25][N:24]=[C:23]([CH3:26])[C:22]=1[CH3:27])(=[O:19])=[O:18].[CH:30](=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C1COCC1>[CH3:6][Si:7]([CH3:28])([CH3:29])[CH2:8][CH2:9][O:10][CH2:11][C:12]1([CH:30]([OH:37])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:16]([S:17]([NH:20][C:21]2[O:25][N:24]=[C:23]([CH3:26])[C:22]=2[CH3:27])(=[O:18])=[O:19])[CH:15]=[CH:14][S:13]1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 22998459HCID 22998459, compoundHCID 178418339Butyllithium

Product 1

HCID 22998524HCID 22998524, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

n-BuLi (2.39M, 177 μl) was slowly added to a solution of (2-trimethylsilylethoxymethyl)-N-(3,4-dimethyl-5-isoxazolyl)thiophene-3-sulfonamide (156 mg, 0.38 mmol) in THF at -78° C. under nitrogen. The reaction was stirred at -78° C. for 45 min., then benzaldehyde (45 μl, 0.42 mmol) was added in one lot at -78° C. and the solution was allowed to come to room temperature. Stirring was continued for 1 hr. Purification was achieved by column chromatography using 10% ethyl acetate/hexanes to give 179 mg 2-[2-(trimethylsilyl)ethoxymethyl]-N-(3,4-dimethyl-5-isoxazolyl)-2-(α-hydroxybenzyl)thiophene-3-sulfonamide as a yellow viscous oil (90% yield).

Workup

  1. customto come to room temperature
  2. stirringStirring
  3. waitwas continued for 1 hr
  4. customPurification

Sources & evidence

ORD record
ord-ddae87565ab74200ac6b6aede231fd14
Source dataset
uspto-grants-1997_01
Patent number
US05594021

Reaction notes

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