Methanesulfonic Acid → Dimethyl (3-oxo-1,3-dihydro-2-benzofuran-1-yl)phosphonate

HRID 269964

反応式

HRID 269964 の反応式
[P:1]([O-:6])([O:4][CH3:5])[O:2][CH3:3].C[O-].[Na+].[C:10]([C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH:15]=O)([OH:12])=[O:11].CS(O)(=O)=O>CO>[CH3:3][O:2][P:1]([CH:15]1[C:14]2[C:13](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10](=[O:12])[O:11]1)(=[O:6])[O:4][CH3:5]

参加物

6

反応物 4

HCID 6395Methanesulfonic AcidHCID 8406Phthalaldehydic acidHCID 10942334Sodium MethoxideHCID 21884954Dimethylphosphite

生成物 1

HCID 11118213Dimethyl (3-oxo-1,3-dihydro-2-benzofuran-1-yl)phosphonate

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

反応条件

温度
20 °C

実験手順

Dimethyl phosphite (22.0 g, 0.2 mol) was added drop-wise to a solution of sodium methoxide (43.0 g) in methanol (100 ml) at 0° C. 2-Carboxybenzaldehyde (21.0 g, 0.1 mol) was then added portion-wise to the reaction mixture as a slurry in methanol (40 ml), with the temperature kept below 5° C. The resulting pale yellow solution was warmed to 20° C. over 1 hour. Methanesulphonic acid (21.2 g, 0.22 mol) was added to the reaction drop-wise and the resulting white suspension was evaporated in vacuo. The white residue was quenched with water and extracted into chloroform (3×100 ml). The combined organic extracts were washed with water (2×100 ml), dried over MgSO4, and evaporated in vacuo to yield (3-oxo-1,3-dihydro-isobenzofuran-1-yl)phosphonic acid dimethyl ester as a white solid (32.0 g, 95%, 95% purity). This was then used without further purification in the next stage.

後処理

  1. customkept below 5° C
  2. customthe resulting white suspension was evaporated in vacuo
  3. customThe white residue was quenched with water
  4. extractionextracted into chloroform (3×100 ml)
  5. washThe combined organic extracts were washed with water (2×100 ml)
  6. dry with materialdried over MgSO4
  7. customevaporated in vacuo

出典と根拠

ORDレコード
ord-6ff759119ac540f0b5fd1dceb834ca69
出典データセット
uspto-grants-2008_11
特許番号
US07449464B2

関連ノート

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