Diisopropylamine → 3-Cyclohexyl-3-hydroxy-1-(2-iodophenyl)propan-1-one

HRID 1774936ノート

反応式

HRID 1774936 の反応式
C(NC(C)C)(C)C.[Li]CCCC.[I:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20](=[O:22])[CH3:21].[CH2:23]1[CH2:28][CH2:27][CH:26]([CH:29]=[O:30])[CH2:25][CH2:24]1>C1COCC1>[CH:26]1([CH:29]([OH:30])[CH2:21][C:20]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[I:13])=[O:22])[CH2:27][CH2:28][CH2:23][CH2:24][CH2:25]1

参加物

6

反応物 4

HCID 7912DiisopropylamineHCID 16275CyclohexanecarboxaldehydeHCID 2404312'-IodoacetophenoneHCID 178418339Butyllithium

生成物 1

HCID 709143663-Cyclohexyl-3-hydroxy-1-(2-iodophenyl)propan-1-one収率 78%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-30 °C

実験手順

To a solution of diisopropylamine (1.6 mL, 11.1 mmol) in THF (38 mL) at 0° C. was added n-BuLi (4.1 mL, 10.2 mmol) under an atmosphere of N2. After 30 min the solution was cooled to −30° C. and a solution of 1-(2-iodophenyl)ethanone (2.27 g, 9.23 mmol) in THF (6 mL) was added dropwise to the mixture and was stirred for 45 min at −30° C. The mixture was cooled to −78° C. and cyclohexylcarboxaldehyde (1.2 mL, 9.69 mmol) was added dropwise and the mixture was allowed to warm to −40° C. over 2 h. The reaction was quenched by the addition of saturated aqueous NH4Cl. The aqueous layer was extracted with EtOAc (2×50 mL). The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated. The residue was purified by flash column chromatography to afford the title compound as yellow oil (2.56 g, 78%). 1H NMR: 1.02-1.27 (m, 4H), 1.41-1.49 (m, 1H), 1.66-1.76 (m, 4H), 1.89 (d, 1H, J=12.4 Hz), 2.88 (d, 1H, J=3.2 Hz), 2.98 (dd, 1H, J=9.2 Hz, 17.2 Hz), 3.13 (dd, 1H, J=2.0 Hz, 17.2 Hz), 3.99-4.01 (m, 1H), 7.11-7.15 (m, 1H), 7.42 (d, 2H, J=4.4 Hz), 7.93 (d, 1H, J=8.0 Hz).

後処理

  1. temperatureThe mixture was cooled to −78° C.
  2. temperatureto warm to −40° C. over 2 h
  3. customThe reaction was quenched by the addition of saturated aqueous NH4Cl
  4. extractionThe aqueous layer was extracted with EtOAc (2×50 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by flash column chromatography

出典と根拠

ORDレコード
ord-3fa1fc75d7204d4e82d0004f652fddaf
出典データセット
uspto-grants-2016_02
特許番号
US09260434B2

反応ノート

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