Chloromethyl Methyl Ether → 7,8-Difluoro-6-methoxymethoxy-2-pentylchroman

HRID 2244839ノート

反応式

HRID 2244839 の反応式
[F:1][C:2]1[C:11]([F:12])=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[O:9]2)=[CH:4][C:3]=1[OH:18].C(N(C(C)C)C(C)C)C.[CH3:28][O:29][CH2:30]Cl.C(N(CC)CC)C>ClCCl.O>[F:1][C:2]1[C:11]([F:12])=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[O:9]2)=[CH:4][C:3]=1[O:18][CH2:28][O:29][CH3:30]

参加物

7

反応物 4

HCID 7864Chloromethyl Methyl EtherHCID 8471TriethylamineHCID 81531DiisopropylethylamineHCID 46834772HCID 46834772、化合物

生成物 1

HCID 592152597,8-Difluoro-6-methoxymethoxy-2-pentylchroman

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

16.9 g (65.9 mmol) of 7,8-difluoro-2-pentylchroman-6-ol are dissolved in 110 ml of dichloromethane, and 13.5 ml (77.1 mmol) of N-ethyldiisopropylamine are added with ice-cooling. After 5 min, 6.0 ml (79.0 mmol) of chloromethyl methyl ether are metered in the temperature range from 15 to 30° C. After 16 h at room temperature, 50 ml of triethylamine are added, and the batch is stirred again for 24 h. Water is added to the reaction mixture, and the organic phase is separated off. The aqueous phase is extracted with dichloromethane, and the combined organic phases are washed successively with water and sat. sodium chloride soln. The solution is dried using sodium sulfate and concentrated to dryness. The crude product is purified by column chromatography (SiO2, 1-chlorobutane), giving 7,8-difluoro-6-methoxymethoxy-2-pentylchroman as a yellowish oil.

後処理

  1. temperaturecooling
  2. customare metered in the temperature range from 15 to 30° C
  3. waitAfter 16 h at room temperature
  4. customthe organic phase is separated off
  5. extractionThe aqueous phase is extracted with dichloromethane
  6. washthe combined organic phases are washed successively with water and sat. sodium chloride soln
  7. customThe solution is dried
  8. concentrationconcentrated to dryness
  9. customThe crude product is purified by column chromatography (SiO2, 1-chlorobutane)

出典と根拠

ORDレコード
ord-d2684f28c73b43cbb22370c06e970e2d
出典データセット
uspto-grants-2010_03
特許番号
US07678929B2

反応ノート

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