Methyl iodide → 2-Methoxy-4-(2-tetrahydropyranyl)oxy-6-methylbenzaldehyde

HRID 1798141ノート

反応式

HRID 1798141 の反応式
[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)[CH:7]=[C:6]([CH3:17])[C:3]=1[CH:4]=[O:5].[H-].[Na+].[CH3:20]I>CN(C=O)C>[CH3:20][O:1][C:2]1[CH:9]=[C:8]([O:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)[CH:7]=[C:6]([CH3:17])[C:3]=1[CH:4]=[O:5]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10823699HCID 10823699、化合物

生成物 1

HCID 107531782-Methoxy-4-(2-tetrahydropyranyl)oxy-6-methylbenzaldehyde

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

An ice-cold yellow solution of 2-hydroxy-6-methyl-4-(tetrahydro-pyran-2-yloxy)-benzaldehyde (7.60 g, 32.17 mmol) in DMF (150 mL), was treated with NaH (0.93 g, 38.63 mmol) in portions over 30 min. The suspension was stirred for 15 min, then methyl iodide (3.0 mL, 48.09 mmol) was added dropwise. The mixture was warmed to rt, stirred for 1 h, then quenched with water and extracted with EtOAc. The extracts were washed with brine, dried (Na2SO4), filtered and concentrated to a yellow liquid. The crude product of 2-methoxy-6-methyl-4-(tetrahydro-pyran-2-yloxy)-benzaldehyde was used in the next step without further purification. 1H NMR (400 MHz, CDCl3) δ 10.49 (s, 1H), 6.50 (s, 1H), 6.49 (s, 1H), 5.54-5.52 (m, 1H), 3.87 (s, 1H), 3.88-3.80 (m, 1H), 3.67-3.61 (m, 1H), 2.57 (s, 3H), 2.10-1.95 (m, 1H), 1.95-1.82 (m, 2H), 1.80-1.58 (m, 3H).

後処理

  1. stirringstirred for 1 h
  2. customquenched with water
  3. extractionextracted with EtOAc
  4. washThe extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated to a yellow liquid
  8. customThe crude product of 2-methoxy-6-methyl-4-(tetrahydro-pyran-2-yloxy)-benzaldehyde was used in the next step without further purification

出典と根拠

ORDレコード
ord-b3021de16a9b4edfafcdb208e452ddda
出典データセット
uspto-grants-2013_01
特許番号
US08343944B2

反応ノート

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