Water → 2-[3-(2,4-Difluorophenyl)sulfanylpropoxy]oxane

HRID 548756

反応式

HRID 548756 の反応式
[H-].[Na+].[F:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[SH:11].Br[CH2:13][CH2:14][CH2:15][O:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][O:18]1.O>C1COCC1>[F:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[S:11][CH2:13][CH2:14][CH2:15][O:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][O:18]1

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27370732,4-Difluorobenzene-1-thiolHCID 27779882-(3-Bromopropoxy)tetrahydro-2H-pyran

生成物 1

HCID 576632252-[3-(2,4-Difluorophenyl)sulfanylpropoxy]oxane収率 77.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Sodium hydride (60% dispersion in mineral oil) (120 mg, 3.01 mmol) was added to a solution of 2,4-difluorothiophenol (0.4 g, 2.74 mmol) in THF (10 mL) at 0° C., under argon. The reaction was allowed to warm to RT and 2-(3-bromopropoxy)tetrahydro-2H-pyran (672 mg, 3.01 mmol) added. The reaction was stirred at RT for 4 hours then poured into iced water (50 mL) and extracted into ethyl acetate (50 mL). The organics were washed with brine (50 mL), dried (MgSO4), filtered and the solvent removed in vacuo to give a yellow oil which was chromatographed on silica, eluting with 0-10% ethyl acetate in isohexane, to give the desired compound as a colourless oil (610 mg). 1H NMR δ (CDCl3): 1.49-1.61 (m, 4H), 1.65-1.73 (m, 1H), 1.75-1.90 (m, 3H), 2.96 (t, 2H), 3.46-3.52 (m, 2H), 3.79-3.87 (m, 2H), 4.55-4.56 (m, 1H), 6.80-6.86 (m, 2H), 7.38-7.44 (m, 1H)

後処理

  1. extractionextracted into ethyl acetate (50 mL)
  2. washThe organics were washed with brine (50 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. customto give a yellow oil which
  7. customwas chromatographed on silica
  8. washeluting with 0-10% ethyl acetate in isohexane

出典と根拠

ORDレコード
ord-625c799b1a68490c8e253edfa9f45702
出典データセット
uspto-grants-2011_05
特許番号
US07943607B2

関連ノート

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