Sulfuric Acid → HCID 69672858、化合物

HRID 63937ノート

反応式

HRID 63937 の反応式
[CH2:1]([O:3][C:4](=[O:22])[CH:5]([C:7]1[C:8]([I:21])=[C:9]2[C:16]3[CH2:17][CH2:18][CH2:19][CH2:20][C:15]=3[S:14][C:10]2=[N:11][C:12]=1[CH3:13])[OH:6])[CH3:2].C(O[C:27]([CH3:30])([CH3:29])[CH3:28])(=O)C.S(=O)(=O)(O)O>ClCCl>[CH2:1]([O:3][C:4](=[O:22])[CH:5]([C:7]1[C:8]([I:21])=[C:9]2[C:16]3[CH2:17][CH2:18][CH2:19][CH2:20][C:15]=3[S:14][C:10]2=[N:11][C:12]=1[CH3:13])[O:6][C:27]([CH3:30])([CH3:29])[CH3:28])[CH3:2]

参加物

5

反応物 3

HCID 1118Sulfuric AcidHCID 10908tert-Butyl acetateHCID 67606534HCID 67606534、化合物

生成物 1

HCID 69672858HCID 69672858、化合物収率 36%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Ethyl-2-[4-iodo-2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridine-3-yl]-2-hydroxyacetate (3 g, 7 mmol) was taken up in 20 mL dichloromethane and tert-butyl acetate (20 mL, 170 mmol) and the mixture coiled to 3° C. in an ice/water bath. Concentrated sulphuric acid (1.14 mL, 21 mmol) was then added dropwise and the mixture allowed to warm to room temperature over 3 hours. The reaction was quenched by the addition of 100 mL of 1M NaOH and 100 mL water and the organic layer separated. The organics were washed with brine (100 mL), dried over MgSO4 and evaporated under reduced pressure. The residue was purified by flash chrmoatography using a gradient of EtOAc in heptane as eluant (0:100 to 30:70) to afford the title compound as a white solid (1.22 g, 36%). 1H NMR (400 MHz, CDCl3) δ 1.20 (t, 3H), 1.23 (s, 9H), 1.81-1.94 (m, 4H), 2.66 (s, 3H), 2.80-2.87 (m, 2H), 3.22-3.31 (m, 2H), 4.10-4.22 (m, 2H), 5.90 (s, 1H).

後処理

  1. customThe reaction was quenched by the addition of 100 mL of 1M NaOH and 100 mL water
  2. customthe organic layer separated
  3. washThe organics were washed with brine (100 mL)
  4. dry with materialdried over MgSO4
  5. customevaporated under reduced pressure
  6. customThe residue was purified by flash chrmoatography

出典と根拠

ORDレコード
ord-e3b27a76eb3944ae9e7ac2b1ce9f8274
出典データセット
uspto-grants-2016_09
特許番号
US09447116B2

反応ノート

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