Tert-Butanesulfinamide → (NE)-N-[1-[tert-butyl(dimethyl)silyl]oxypropan-2-ylidene]-2-methylpropane-2-sulfinamide

HRID 709905ノート

反応式

HRID 709905 の反応式
[Si:1]([O:8][CH2:9][C:10](=O)[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:13][C:14]([S:17]([NH2:19])=[O:18])([CH3:16])[CH3:15]>C1COCC1.[Cl-].[Na+].O>[Si:1]([O:8][CH2:9]/[C:10](=[N:19]/[S:17]([C:14]([CH3:16])([CH3:15])[CH3:13])=[O:18])/[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

参加物

5

反応物 2

HCID 3382465Tert-ButanesulfinamideHCID 41249691-(tert-Butyldimethylsilyloxy)-2-propanone

生成物 1

HCID 87388767(NE)-N-[1-[tert-butyl(dimethyl)silyl]oxypropan-2-ylidene]-2-methylpropane-2-sulfinamide収率 65.2%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
70 °C

実験手順

1-(tert-butyldimethylsilyloxy)propan-2-one (188 mg, 1.0 mmol) and Ti(OEt)4 (0.52 mL, 2.5 mmol) were dissolved in THF (5 mL). Then 2-methylpropane-2-sulfinamide (121 mg, 1.0 mmol) was added to the mixture under nitrogen atmosphere. The mixture was heated to 70° C. for 2 h. The mixture was poured into brine and filtered through a plug of Celite. The organic layer was concentrated and purified by silica gel chromatography using PE/EA (5/1) to give product the title compound (190 mg, 65%). EDI-MS (M+1): 292. 1H NMR (300 MHz, CDCl3) δ 4.152 (s, 2H), 2.248 (s, 3H), 1.156 (s, 9H), 0.839 (s, 9H), 0.001 (s, 6H).

後処理

  1. filtrationfiltered through a plug of Celite
  2. concentrationThe organic layer was concentrated
  3. custompurified by silica gel chromatography

出典と根拠

ORDレコード
ord-9b4c2d69a23f465c9f27f59b4098b06c
出典データセット
uspto-grants-2015_11
特許番号
US09181191B2

反応ノート

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