Methyl iodide → HCID 59774928、化合物

HRID 2422490ノート

反応式

HRID 2422490 の反応式
[CH3:1][Si:2]([C:5]#[C:6][C:7]1([OH:13])[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1)([CH3:4])[CH3:3].[H-].[Na+].I[CH3:17]>C1COCC1.CN(C=O)C>[CH3:17][O:13][C:7]1([C:6]#[C:5][Si:2]([CH3:3])([CH3:4])[CH3:1])[CH2:8][CH2:9][O:10][CH2:11][CH2:12]1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 597748684-[2-(Trimethylsilyl)ethynyl]oxan-4-ol

生成物 1

HCID 59774928HCID 59774928、化合物

試薬・触媒・溶媒 1

HCID 21974620tetrahydrofuran N,N-dimethylformamide溶媒

実験手順

To a cooled solution (0° C.) of 4-{(trimethylsilyl)ethynyl}tetrahydropyran-4-ol prepared as described in the above example (2.5 g, 12.6 mmol) in a THF-DMF mixture (55 mL, 10:1), sodium hydride (60% suspension in oil, 0.504 g, 12.6 mmol) was added portionwise. After addition, the mixture was stirred 15 minutes before iodomethane (0.788 mL, 12.6 mmol) was added. The temperature was slowly raised to room temperature and the reaction was stirred for another 2 hours. The reaction mixture was then quenched with water and the product was extracted with ethyl acetate (2×). The combined organic layers were diluted with hexanes and washed with water and brine, dried over MgSO4, filtered and concentrated. The crude residue obtained was purified by column chromatography (acetone/dichloromethane, 2:98) to afford the title compound. 1H NMR (400 MHz, acetone-d6): 3.82-3.74 (m, 2H), 3.61-3.54 (m, 2H), 3.34 (s, 3H), 1.90-1.82 (m, 2H), 1.71-1.63 (m, 2H), 0.21 (s, 9H).

後処理

  1. additionwas added portionwise
  2. additionAfter addition
  3. additionwas added
  4. customThe reaction mixture was then quenched with water
  5. extractionthe product was extracted with ethyl acetate (2×)
  6. additionThe combined organic layers were diluted with hexanes
  7. washwashed with water and brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude residue obtained
  12. customwas purified by column chromatography (acetone/dichloromethane, 2:98)

出典と根拠

ORDレコード
ord-11a7fcd3a91b49c2a3a05e7d2a1e60ea
出典データセット
uspto-grants-2011_06
特許番号
US07960409B2

反応ノート

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