Triethylamine → HCID 68522073, compound

HRID 2247670Notes

Reaction equation

HRID 2247670 reaction equation
[Si:1]([O:8][CH:9]1[C:14]2[CH:15]=[C:16]([CH:18]=O)[S:17][C:13]=2[CH2:12][CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Cl.NO.C([N:25](CC)CC)C.C1(N=C=NC2CCCCC2)CCCCC1>>[Si:1]([O:8][CH:9]1[C:14]2[CH:15]=[C:16]([C:18]#[N:25])[S:17][C:13]=2[CH2:12][CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 443297Hydroxyamine hydrochlorideHCID 86620216HCID 86620216, compound

Product 1

HCID 68522073HCID 68522073, compound

Procedure

The crude product of the title compound was synthesized by conducting the similar reaction to that mentioned in Example 1 (1c) using 4-{[t-butyl(dimethyl)silyl]oxy}-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxaldehyde (4.4 g, 15.3 mmol) that was obtained in Example 8 (8c), hydroxylamine hydrochloride (1.1 g, 16 mmol), triethylamine (4.1 ml, 30 mmol), and N,N′-dicyclohexylcarbodiimide (3.4 g, 16 mmol). Subsequently, the crude product of the title compound thus obtained was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (1:9) as the eluent to afford the title compound (4.1 g) in a yield of 94% as a colourless oily product.

Workup

  1. customthe similar reaction to

Sources & evidence

ORD record
ord-4977625f8261426caae3a6edd390cb92
Source dataset
uspto-grants-2010_03
Patent number
US07687491B2

Reaction notes

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