Sodium hydride → HCID 68290898、化合物

HRID 72948

反応式

HRID 72948 の反応式
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH3:12].[H-].[Na+].[O:15]1[CH2:18][CH:17](O)[CH2:16]1>CN(C=O)C>[CH3:12][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:2]=1[O:1][CH:17]1[CH2:18][O:15][CH2:16]1)[C:6]([O:8][CH3:9])=[O:7]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 9942117Oxetan-3-olHCID 11240684Methyl 4-hydroxy-3-methylbenzoate

生成物 1

HCID 68290898HCID 68290898、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To methyl 4-hydroxy-3-methyl-benzoate (498 mg, 3 mmol) was added DMF (3 mL) and sodium hydride (240 mg, 6.0 mmol) followed by oxetan-3-ol (445 mg, 6 mmol) and the reaction mixture was heated at 80° C. for 4 hours. The reaction was cooled and quenched with brine solution and extracted with EtOAc (3×10 mL). The organic layer was separated and dried over sodium sulfate and evaporated to give methyl 3-methyl-4-(oxetan-3-yloxy)benzoate. To methyl 3-methyl-4-(oxetan-3-yloxy)benzoate was added sodium hydroxide (3 mL of 1 M NaOH, 3 mmol) solution and the reaction mixture was stirred for 1 hour. The reaction was acidified with 1 M HCl solution to pH 3 and extracted with EtOAc. The organics were separated and dried and concentrated in vacuo to give 3-methyl-4-(oxetan-3-yloxy)benzoic acid. ESI-MS m/z calc. 208.1. Found 209.3 (M+1)+; Retention time: 1.04 minutes (3 min run).

後処理

  1. temperatureThe reaction was cooled
  2. customquenched with brine solution
  3. extractionextracted with EtOAc (3×10 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. customevaporated

出典と根拠

ORDレコード
ord-7f40acac26904302b9713a19c1196cee
出典データセット
uspto-grants-2014_09
特許番号
US08828996B2

関連ノート

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