2-Chloromethyl 2-(trimethylsilyl)ethyl ether → HCID 58000310、化合物

HRID 1392219ノート

反応式

HRID 1392219 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2([C:18]3[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=3[F:25])[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[CH3:36][Si:37]([CH3:44])([CH3:43])[CH2:38][CH2:39][O:40][CH2:41]Cl>O1CCCC1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([C:11]2([C:18]3[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=3[F:25])[CH2:16][CH2:15][C:14](=[O:17])[CH:13]([CH2:41][O:40][CH2:39][CH2:38][Si:37]([CH3:44])([CH3:43])[CH3:36])[CH2:12]2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 2733832Lithium HexamethyldisilazideHCID 104301374-(4-chlorophenyl)sulfonyl-4-(2,5-difluorophenyl)cyclohexan-1-one

生成物 1

HCID 58000310HCID 58000310、化合物収率 44.8%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

4-[(4-Chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)cyclohexanone (WO 02/081435) (2.0 g, 5.2 mmol) in dry tetrahydrofuran (10 mL) was added dropwise to a cooled solution of 0.5 M lithium hexamethyldisilazide in tetrahydrofuran (11.4 mL) at −78° C. The mixture was stirred at this temperature for 2 hours before adding 2-(trimethylsilyl)ethoxymethyl chloride (1.4 mL, 7.8 mmol) and the solution allowed to warm to rt. over 16 hours. The reaction mixture was diluted with ethyl acetate (10 mL), washed with water (10 mL), and the organic phase separated, dried (MgSO4) and evaporated to dryness. The product was purified on silica eluting with [9:1] hexane-ethyl acetate to yield 1.2 g of the title compound. 1H NMR CDCl3 7.38 (4H, s), 7.24-7.16 (1H, m), 7.12-7.06 (1H, m), 6.97-6.87 (1H, m), 3.66 (1H, dd, J=9.7 and 3.0 Hz), 3.51-3.45 (3H, m), 3.17-3.15 (1H, m), 3.05-2.98 (1H, m), 2.56-2.49 (2H, m), 241-2.35 (2H, m), 2.23-2.17 (1H, m), 0.91-0.87 (2H, m) and 0.03 (9H, s).

後処理

  1. waitover 16 hours
  2. washwashed with water (10 mL)
  3. customthe organic phase separated
  4. dry with materialdried (MgSO4)
  5. customevaporated to dryness
  6. customThe product was purified on silica eluting with [9:1] hexane-ethyl acetate

出典と根拠

ORDレコード
ord-481ac11207b247e5a0b4ebd026971896
出典データセット
uspto-grants-2008_03
特許番号
US07342009B2

反応ノート

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