Dimethylformamide → HCID 20768134、化合物

HRID 1991145ノート

反応式

HRID 1991145 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([CH3:16])[CH:10]=2)=[CH:4][C:3]=1[CH3:17].C([O-])([O-])=O.[Cs+].[Cs+].CN(C=O)C.Br[CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32]>O>[C:34]([O:33][C:31](=[O:32])[CH2:30][O:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([CH3:16])[CH:10]=2)=[CH:4][C:3]=1[CH3:17])([CH3:37])([CH3:36])[CH3:35]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 618879Bis(4-hydroxy-3-methylphenyl) Sulfide

生成物 1

HCID 20768134HCID 20768134、化合物

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

An oven-dried 100 mL round-bottomed flask was charged with bis-(4-hydroxy-3-methylphenyl)-sulfide (8.6 g, 34.9 mmol), finely powdered Cs2CO3 (11.9 g, 36.7 mmol), and anhydrous DMF (35 mL). Next, tert-butyl bromoacetate (5.2 mL, 34.9 mmol, Aldrich) was added dropwise, and the reaction was stirred vigorously overnight at room temperature. The reaction was poured into 500 mL of water and extracted with 3×50 mL of methylene chloride. The combined organics were washed with 2×150 mL of water, dried over Na2SO4, and concentrated to a slightly yellow oil. The mixture was then purified by flash chromatography (SiO2 gel 60, eluted with 10% hexanes in DCM-5% hexanes in DCM-100% DCM). The fractions containing only desired product 1.1 were combined and concentrated to a white solid (3.5 g). The mixed fractions were combined, concentrated, and resubjected to the same chromatography conditions to yield an additional 2.0 g of pure 1.1. 1H NMR (400 MHz) (CDCl3) δ 7.13 (2H, m); 7.06 (2H, m); 6.70 (1H, d, J=8.3 Hz); 6.59 (1H, d, J=8.4 Hz); 4.50 (2H, s); 2.23 (3H, s); 2.20 (3H, s); 1.48 (9H, s).

後処理

  1. extractionextracted with 3×50 mL of methylene chloride
  2. washThe combined organics were washed with 2×150 mL of water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to a slightly yellow oil
  5. customThe mixture was then purified by flash chromatography (SiO2 gel 60, eluted with 10% hexanes in DCM-5% hexanes in DCM-100% DCM)
  6. additionThe fractions containing only desired product 1.1
  7. concentrationconcentrated to a white solid (3.5 g)
  8. concentrationconcentrated
  9. customto yield an additional 2.0 g of pure 1.1

出典と根拠

ORDレコード
ord-00dd260f47274927a9b9b6bcfb6c9ec4
出典データセット
uspto-grants-2010_01
特許番号
US07645779B2

反応ノート

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