Sodium Sulfite → HCID 178472369、化合物

HRID 928103ノート

反応式

HRID 928103 の反応式
[Br:1][C:2]1[S:6][C:5]([CH:7]([OH:19])[C@H:8]2[CH2:13][CH2:12][C@H:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:10][CH2:9]2)=[N:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+].S([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Br:1][C:2]1[S:6][C:5]([C:7]([C@H:8]2[CH2:9][CH2:10][C@H:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:12][CH2:13]2)=[O:19])=[N:4][CH:3]=1

参加物

6

反応物 4

HCID 24437Sodium SulfiteHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 178472370HCID 178472370、化合物

生成物 1

HCID 178472369HCID 178472369、化合物収率 97%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Ethyl trans-4-[(5-bromo-1,3-thiazol-2-yl)(hydroxy)methyl]cyclohexanecarboxylate (11.5 g, 33 mmol) was diluted with CH2Cl2 (115 mL) and immersed in a room temperature water bath. To this was added Dess-Martin periodinane (15.4 g, 36.3 mmol) resulting in a noticeable exotherm. After 30 min, an aqueous solution of 5% NaHCO3 and 5% sodium sulfite was added and the resulting biphasic mixture stirred until both layers were clear. The layers were separated, the aqueous layer back extracted with CH2Cl2 and the combined organics dried with MgSO4, filtered and concentrated in vacuo. The crude residue was absorbed on silica and purified by flash chromatography to afford ethyl trans-4-[(5-bromo-1,3-thiazol-2-yl)carbonyl]cyclohexane-carboxylate (11.1 g, 32 mmol) as a yellow oil. MS ESI calc'd. for C13H17BrNO3S [M+H]+ 346, 348. found 346, 348. 1H NMR (600 MHz, CDCl3) δ 7.82 (s, 1H), 4.14-4.03 (m, 2H), 3.53-3.41 (m, 1H), 2.35-2.21 (m, 1H), 2.15-1.96 (m, 4H), 1.61-1.43 (m, 4H), 1.21 (t, J=7.1, 3H).

後処理

  1. customimmersed in a room temperature
  2. customresulting in a noticeable exotherm
  3. customThe layers were separated
  4. extractionthe aqueous layer back extracted with CH2Cl2
  5. dry with materialthe combined organics dried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was absorbed on silica
  9. custompurified by flash chromatography

出典と根拠

ORDレコード
ord-838a661bfd6c42c2b71979fc27840187
出典データセット
uspto-grants-2016_03
特許番号
US09290490B2

反応ノート

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