Ethyl Bromide → 4-Methoxyimino-5-methyl-6-bromothiochroman

HRID 1458254ノート

反応式

HRID 1458254 の反応式
[CH3:1][O:2][N:3]=[C:4]1[C:13]2[C:8](=[C:9](C)[CH:10]=[C:11](C(C3C=NN(CC)C=3OS(CCC)(=O)=O)=O)[C:12]=2[CH3:14])[S:7](=O)(=O)[CH2:6][CH2:5]1.[Mg].C([Br:37])C.CON=C1C2C(=CC=C(C3C=NN(CC)C=3OS(CCC)(=O)=O)C=2C)S(=O)(=O)C(=C=O)C1>C1COCC1>[CH3:1][O:2][N:3]=[C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([Br:37])[C:12]=2[CH3:14])[S:7][CH2:6][CH2:5]1

参加物

6

反応物 4

HCID 6332Ethyl BromideHCID 5462224MagnesiumHCID 537956584-Methoxyimino-5,8-dimethyl-6-(1-ethyl-5-n-propanesulfonyloxypyrazol-4-yl)carbonylthiochroman-1,1-dioxideHCID 867526644-Methoxyimino-5-methyl-6-(1-ethyl-5-n-propanesulfonyloxypyrazol-4-yl)-carbonylthiochroman-1,1-dioxide

生成物 1

HCID 543825024-Methoxyimino-5-methyl-6-bromothiochroman

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

3.0 Grams (12 mmol) of 5-methyl-6-bromothiochroman-4-one and 1.9 g (23 mmol) of O-methylhydroxylamine hydrochloride were refluxed in a solvent mixture of 10 ml of ethanol and 10 ml of pyridine under heat for 30 minutes. The solvents were distilled off under reduced pressure, 50 ml of 5% hydrochloric acid was added, and a formed solid was recovered by filtration, washed with water and then dried to give 3.2 g (yield 93%) of 4-methoxyimino-5-methyl-6-bromothiochroman. (2) 1.1 Grams (46 mmol) of magnesium was dispersed in 10 ml of THF, and 2.2 g (20 mmol) of ethyl bromide was dropwise added under nitrogen current. The mixture was allowed to react for 10 minutes, and then a THF solution of 2.9 g (10 mmol) of the 4-methoxyimino-5-methyl-6-bromothiochroman obtained in the above (1) was gradually added at room temperature. The mixture was refluxed for 3 hours and then cooled to room temperature, and carbon dioxide gas was bubbled in for 1 hour. To the reaction mixture was added 5% hydrochloric acid, and the mixture was extracted with ether. An ether layer was extracted with a 5% potassium carbonate aqueous solution, and an aqueous layer was neutralized with concentrated hydrochloric acid. The neutralization product was extracted with ethyl acetate, and the extract was washed with a saturated sodium chloride aqueous solution. The washed extract was dried over sodium sulfate, and then the solvent was distilled off to give 1.6 g (yield 63%) of 4-methoxyimino-5-methylthiochroman-6-carboxylic acid.

後処理

  1. customto react for 10 minutes

出典と根拠

ORDレコード
ord-e577b516f0f341d59fc6d2bb729ef5f4
出典データセット
uspto-grants-1998_12
特許番号
US05849926

反応ノート

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