Benzaldehyde → HCID 22998524, compound

HRID 2270719Notes

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

Conditions

Temperature: -78 °C

Procedure

n-BuLi (2.39 M, 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-(a-hydroxybenzyl)thiophene-3-sulfonamide as a yellow viscous oil (90% yield).

Workup

customto come to room temperature
stirringStirring
waitwas continued for 1 hr
customPurification

Sources & evidence

ORD record: ord-a1613987f2eb40c4aad18c03671112a3
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06331637B1

Reaction notes

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